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1-(1-bromoethyl)-4-fluorobenzene

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1-(1-bromoethyl)-4-fluorobenzene Basic information
Product Name:1-(1-bromoethyl)-4-fluorobenzene
Synonyms:4-FLUOROPHENETHYL BROMIDE;4-FLUORO-1-(2-BROMOETHYL)BENZENE;1-FLUORO-4-(2-BROMOETHYL)BENZENE;2-(4-FLUOROPHENYL)ETHYL BROMIDE;1-BROMO-2-(4-FLUOROPHENYL)ETHANE;1-(1-Bromoethyl)-4-fluorobenzene;1-(4-Fluorophenyl)ethyl bromide;1-Bromo-1-(4-fluorophenyl)ethane
CAS:65130-46-3
MF:C8H8BrF
MW:203.05
EINECS:
Product Categories:Fluorine series
Mol File:65130-46-3.mol
1-(1-bromoethyl)-4-fluorobenzene Structure
1-(1-bromoethyl)-4-fluorobenzene Chemical Properties
Boiling point 100-104 °C15 mm Hg(lit.)
density 1.4498 g/mL at 25 °C(lit.)
refractive index n20/D 1.534(lit.)
Fp 200 °F
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
form oil
color Colourless
Safety Information
Hazard Codes Xn,N
Risk Statements 22-51/53
Safety Statements 61
WGK Germany 2
Hazard Note Harmful
HS Code 2903998090
MSDS Information
ProviderLanguage
SigmaAldrich English
1-(1-bromoethyl)-4-fluorobenzene Usage And Synthesis
Synthesis
1-(4-Fluorophenyl)ethanol

403-41-8

1-(1-bromoethyl)-4-fluorobenzene

65130-46-3

General procedure for the synthesis of 1-(1-bromoethyl)-4-fluorobenzene from 1-(4-fluorophenyl)-1-ethanol: 1-(4-fluorophenyl)ethanol (0.455 mL, 3.57 mmol) was mixed with phosphorus tribromide (0.673 mL, 7.13 mmol) in chloroform (10 mL) and heated to a temperature of 70°C for 3 days. Upon completion of the reaction, the reaction mixture was quenched by pouring it into ice water and diluted with ethyl acetate. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuum to obtain the crude product. The crude product was purified by silica gel column chromatography with hexane/dichloromethane (2:1) as eluent to afford 1-(1-bromoethyl)-4-fluorobenzene (154 mg, 0.758 mmol, 21.3% yield) as a colorless oil.1H NMR (400 MHz, CDCl3) δ 7.49-7.40 (m, 2H), 7.09-7.00 (m , 2H), 5.23 (q, J = 7.0 Hz, 1H), 2.06 (d, J = 6.8 Hz, 3H).

References[1] Journal of the American Chemical Society, 2016, vol. 138, # 34, p. 10774 - 10777
[2] Patent: US2012/46301, 2012, A1. Location in patent: Page/Page column 30; 31
[3] Patent: WO2018/148626, 2018, A1. Location in patent: Page/Page column 152
[4] Tetrahedron, 1977, vol. 33, p. 1581 - 1585
[5] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1984, vol. 23, # 1, p. 60 - 62
1-(1-bromoethyl)-4-fluorobenzene Preparation Products And Raw materials
Raw materials1-(4-Fluorophenyl)ethanol-->1-Ethyl-4-fluorobenzene-->3-Bromo-alpha-methylbenzyl alcohol-->Phosphorus tribromide-->Chloroform
Tag:1-(1-bromoethyl)-4-fluorobenzene(65130-46-3) Related Product Information
(2-Bromoethyl)benzene N1-(2-Bromoethyl)-4-fluorobenzene-1-sulphonamide N1-(2-Bromoethyl)-4-fluorobenzene-1-sulfonamide 3-Fluorophenethyl bromide 1-(2-Bromoethyl)-4-fluorobenzene (1-Bromoethyl)benzene