Boron tribromide → 4-(chloromethyl)-2,6-dimethylphenol

HRID 864379Notes

Reaction equation

HRID 864379 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:12])[C:9]=1[O:10]C)[CH2:5][Cl:6].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:12][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([CH3:1])[C:9]=1[OH:10])[CH2:5][Cl:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 194187982,6-Dimethyl-4-(chloromethyl)anisole

Product 1

HCID 2786614-(chloromethyl)-2,6-dimethylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dimethyl-4-methoxybenzyl chloride (I, PREPARATION 4, 1.8 g) is added to a solution of boron tribromide (1.5 m) in dichloromethane (70 ml) at 78°. The solution is allowed gradually to warm to 20°-25° overnight. The reaction is poured into an aqueous sodium bicarbonate solution, and the phases are separated. The dichloromethane phase is washed once with water and then with concentrated hydrochloric acid. The dried (sodium sulfate) organic phase is concentrated under reduced pressure to give the title compound.

Workup

  1. temperatureto warm to 20°-25° overnight
  2. customthe phases are separated
  3. washThe dichloromethane phase is washed once with water
  4. dry with materialThe dried (sodium sulfate) organic phase
  5. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-67a4c4561dc345898bc20bd3eb8b8398
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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