Carbon tetrabromide → 2-(3,5-Dimethoxyphenylthio)benzyl bromide

HRID 567878Notes

Reaction equation

HRID 567878 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14]O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][Br:40])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 118079672-(3,5-Dimethoxyphenylthio)benzyl alcohol

Product 1

HCID 155124432-(3,5-Dimethoxyphenylthio)benzyl bromideYield 98.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3,5-Dimethoxyphenylthio)benzyl alcohol (7.9 g) was dissolved in methylene chloride (40 ml), then triphenylphosphine (11.2 g) and carbon tetrabromide (11.2 g) were added thereto, the mixture was stirred at room temperature for ten minutes, diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=5:1) to give 2-(3,5-dimethoxyphenylthio)-benzyl bromide (9.53 g, yield of 98%).

Workup

  1. washwashed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9ab92f325fdf41a9bf0b77c89064fe5c
Source dataset
uspto-grants-2001_01
Patent number
US06180659B2

Reaction notes

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