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

HRID 859659Notes

Reaction equation

HRID 859659 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[Br:25][C:26]1[CH:31]=[CH:30][C:29](CO)=[C:28]([CH3:34])[CH:27]=1>C(Cl)Cl>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:20][Br:24])=[C:28]([CH3:34])[CH:27]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzeneYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (11.35 g, 43.27 mmol) followed by carbon tetrabromide (14.35 g, 43.27 mmol) were added to a solution of (4-bromo-2-methyl-phenyl)-methanol (7.25 g, 36 mmol) in CH2Cl2 (200 mL). The mixture was stirred at room temperature for 5 hours. The solution was concentrated to 15 mL. The residue was purified by flash column chromotography (1% to 10% EtOAc in Hexane) gave the product as brown oil (9.25 g, 81% yield). 1H NMR (400 MHz, CDCl3) δ: 2.39 (3 H, s) 4.45 (2 H, s) 7.17 (1 H, d, J=8.08 Hz) 7.29 (2 H, m) 7.30 (1 H, dd, J=8.08, 2.02 Hz) 7.34 (1 H, s).

Workup

  1. concentrationThe solution was concentrated to 15 mL
  2. customThe residue was purified by flash column chromotography (1% to 10% EtOAc in Hexane)

Sources & evidence

ORD record
ord-2df04d3cf0c4489fbf67396dc24b5f99
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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