Chloroform → 3-(2-Bromoethyl)phenol

HRID 220329Notes

Reaction equation

HRID 220329 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10]C)[CH:5]=1.C(Cl)(Cl)Cl.B(Br)(Br)Br.[NH4+].[OH-]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 1374501-Bromo-2-(3-methoxyphenyl)ethane

Product 1

HCID 5723003-(2-Bromoethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 1-(2-bromoethyl)-3-methoxybenzene (1.00 g, 4.7 mmol) in CHCl3 (50 mL, 0.6 mol) was cooled to at 0° C. 1.0 M of BBr3 in DCM (27.9 mL) was cooled to 0° C. and added to the solution. The solution was allowed to warm to 30° C. over 30 minutes, then was poured into a solution of ice and 30% NH4OH, which was stirred at 0° C. for 30 minutes. The organic layer was taken and concentrated with no reduced pressure.

Workup

  1. additionadded to the solution
  2. concentrationconcentrated with no reduced pressure

Sources & evidence

ORD record
ord-cb8ad710095c4f8b858d8eeabae7f451
Source dataset
uspto-grants-2012_06
Patent number
US08202891B2

Reaction notes

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