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

HRID 419966Notes

Reaction equation

HRID 419966 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>ClCCl>[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 129%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-bromo-2-chlorophenyl)methanol (4.34 g, 19.6 mmol) in dichloromethane (98 mL) at 0° C. is added carbon tetrabromide (6.5 g, 19.6 mmol) and triphenylphosphine (5.14 g, 19.6 mmol). The reaction mixture is stirred 16 h at room temperature. Then, the solvent is removed and the crude solid suspended in hexanes/EtOAc 9:1 (100 mL) and filtered on a silica gel pad. The pad is rinsed with hexanes/EtOAc 9:1 (100 mL) and the filtrate is concentrated in vacuo to provide the expected product 4-bromo-1-(bromomethyl)-2-chlorobenzene (7.19 g, 129%) contaminated with bromoform. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.57 (1H, d, J=2.0 Hz), 7.39 (1H, dd, J=8.2, 2.0 Hz), 7.30 (1H, d, J=8.2 Hz), 4.53 (2H, s).

Workup

  1. customThen, the solvent is removed
  2. filtrationfiltered on a silica gel pad
  3. washThe pad is rinsed with hexanes/EtOAc 9:1 (100 mL)
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-9ce9642e44e148cfa1c7ffd2357ae1bc
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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