Carbon tetrabromide → 2-((5-(Bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene

HRID 337250Notes

Reaction equation

HRID 337250 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14]O)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:22][CH2:14][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([CH:7]=1)[O:5][CH2:4][C:3]1[C:2]([CH3:1])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:20]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66959381(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)methanol

Product 1

HCID 669586602-((5-(Bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(2,6-dimethylbenzyloxy)-4-methoxyphenyl)methanol (Step C, 5.23 g, 20.4 mmol) and CBr4 (10.16 g, 30.6 mmol) in dry CH2Cl2 (20 ml) was added portion wise triphenylphosphine (8.03 g, 30.64 mmol) at 0° C. The reaction mixture was stirred for 1.5 hours, filtered, concentrated and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-c40a8a4e4f4b45ca8f2430e050286e3f
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

Loading…