Carbon tetrabromide → 1-(Bromomethyl)-3-nitro-5-(trifluoromethyl)benzene

HRID 1640130Notes

Reaction equation

HRID 1640130 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14]O)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 186217851-(Bromomethyl)-3-nitro-5-(trifluoromethyl)benzeneYield 689%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (13.15 g, 59.5 mmol) in DCM (200 mL) at 0° C. was added PPh3 (18.7 g, 71.4 inmol) and CBr4 (21.7 g, 65.4 mmol). The reaction mixture was allowed to stir and warm to rt overnight. The reaction mixture was poured directly onto a pad of silica and the eluant was concentrated to give 1-(bromomethyl)-3-nitro-5-(trifluoromethyl)benzene as a yellow oil (40 g, 689%).

Workup

  1. additionThe reaction mixture was poured directly onto a pad of silica
  2. concentrationthe eluant was concentrated

Sources & evidence

ORD record
ord-9580e81af5664df2868b5ce89119a969
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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