Carbon tetrabromide → 4-(Bromomethyl)-2,6-dimethylphenyl acetate

HRID 43290Notes

Reaction equation

HRID 43290 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12]O)=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2].[Br:15]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12][Br:15])=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 280655654-(Hydroxymethyl)-2,6-dimethylphenyl acetate

Product 1

HCID 132969354-(Bromomethyl)-2,6-dimethylphenyl acetateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of commercially available 4-(hydroxymethyl)-2,6-dimethylphenyl acetate (1 g, 5.15 mmol) and perbromomethane (2.39 g, 7.21 mmol) in tetrahydrofuran (25 mL) was added triphenylphosphine (1.620 g, 6.18 mmol). The mixture was stirred at room temperature for 6 hours then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1) to provide the title compound (1.05 g, 80% yield). MS (DCI/NH3) m/z 274 (M+NH4)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-316f60850f8944f7a843c8241538bade
Source dataset
uspto-grants-2013_09
Patent number
US08536336B2

Reaction notes

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