Carbon tetrabromide → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

HRID 859719Notes

Reaction equation

HRID 859719 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([Cl:10])[CH:3]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:12])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirring solution of (4-bromo-2-chloro-phenyl)-methanol (2.80 g, 12.67 mmol) from step 1 above in CH2Cl2 (60.0 mL) under argon at 0° C., was added carbon tetrabromide (4.41 g, 13.30 mmol) followed by triphenylphosphine (3.48 g, 13.30 mmol). The resulting mixture was stirred for 4 hours at room temperature. The resulting reaction mixture was concentrated in vacuo and the crude residue was purified by flash column chromatography (10% EtOAc in Hexanes) to yield the intermediate bromide as a clear oil (3.59 g, 100%). 1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 7.29 (d, J=8.2 Hz, 1H), 7.39 (dd, J=8.2, 1.9 Hz, 1 H), 7.56 (d, J=1.9 Hz, 1H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customthe crude residue was purified by flash column chromatography (10% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-143e57508ead44a3a1410cdb3b895143
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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