Hydrogen Bromide → 1-(2-Bromoethyl)-4-chlorobenzene

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.[BrH:11]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Br:11])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 18825Benzenemethanol, 4-chloro-alpha-methyl-

Product 1

HCID 230291-(2-Bromoethyl)-4-chlorobenzene

Procedure

In a 65 mL glass pressure vessel, 4-chlorophenylethanol (32.725 g, 209 mmol) was warmed to between 90 and 100° C. The vessel was charged with hydrogen bromide gas and the mixture was stirred at +1.38 to +1.93 bar for 4.5 h. The pressure was released and the reaction showed 99.18% conversion by HPLC. The mixture was allowed to cool to room temperature to leave 2-(4-chlorophenyl)ethyl bromide as a brown liquid (53.735 g).

Sources & evidence

ORD record: ord-4d1a51bd11334accb7757aef65b5f025
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822727B2

Reaction notes

Loading…