Carbon tetrabromide → 1-(Bromomethyl)-3-(2,6-dimethylbenzyloxy)-2-methylbenzene

HRID 337265Notes

Reaction equation

HRID 337265 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:14])=[C:8]([CH2:12]O)[CH:9]=[CH:10][CH:11]=1.C(Br)(Br)(Br)[Br:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:21][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:2]([CH3:1])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:19])[C:7]=1[CH3:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66959083(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)methanol

Product 1

HCID 669593551-(Bromomethyl)-3-(2,6-dimethylbenzyloxy)-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(2,6-dimethylbenzyloxy)-2-methylphenyl)methanol (Step C, 3.68 g, 14.37 mmol) and CBr4 (5.25 g, 15.8 mmol) in dry CH2Cl2 (20 ml) was added portion wise triphenylphosphine (4.14 g, 15.8 mmol) at 0° C. The reaction mixture was stirred for 4 hours, filtered, concentrated and purified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1) to give the title compound. The solid was further kept under vacuum for 6 hours to dry.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1)

Sources & evidence

ORD record
ord-61ea3bb2aea14e2c945b87a8853c0d34
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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