Dimethylformamide → 1-Benzyloxy-2-bromomethyl-4-methoxymethoxybenzene

HRID 1294104Notes

Reaction equation

HRID 1294104 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41].CN(C)C=O>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19][Br:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17861294(2-Benzyloxy-5-methoxymethoxyphenyl)methanol

Product 1

HCID 178613821-Benzyloxy-2-bromomethyl-4-methoxymethoxybenzeneYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2-benzyloxy-5-methoxymethoxyphenyl)methanol (8.0 g), triphenylphosphine (7.66 g), carbon tetrabromide (9.68 g) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 1.5 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (4.49 g, 46%) of 1-benzyloxy-2-bromomethyl-4-methoxymethoxybenzene from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 55-57° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a0f0ce059a04d9baafc6d631cf898c0
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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