Carbon tetrabromide → 1-(1-Bromoethyl)-4-(trifluoromethoxy)benzene

HRID 594310Notes

Reaction equation

HRID 594310 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH3:11])=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=1)[CH3:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20376123alpha-Methyl-4-(trifluoromethoxy)benzenemethanol

Product 1

HCID 129473941-(1-Bromoethyl)-4-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-(trifluoromethoxy)phenyl)ethanol (150 mg; 0.72 mmol) in anh. DCM (5 ml) was treated at rt with CBr4 (241 mg; 0.72 mmol), and with PPh3 (190 mg; 0.72 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 16 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 1-(1-bromoethyl)-4-(trifluoromethoxy)benzene as a colorless oil which was directly used for the next reaction.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-c97db8d8e6b4490984e4fd8ffa6a5378
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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