Water → 3,4-Bis(benzoyloxymethyl)benzyl bromide

HRID 584291Notes

Reaction equation

HRID 584291 reaction equation
[C:1]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](CO)=[CH:13][C:12]=1[CH2:19][O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Br)(Br)(Br)[Br:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>ClCCl>[C:21]([O:20][CH2:19][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][C:11]=1[CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:29][Br:30])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 697922262-Benzoyloxymethyl-4-hydroxymethylbenzyl benzoate

Product 1

HCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

40 g (106 mmol) of 2-benzoyloxymethyl-4-hydroxymethylbenzyl benzoate are placed in 500 ml of dichloromethane and 77.6 g (234 mmol) of carbon tetrabromide in a round-bottomed flask and under a stream of nitrogen. At 0° C., a solution of 61.3 g (233 mmol) of triphenylphosphine in 200 ml of dichloromethane is added dropwise. The mixture is allowed to warm to room temperature over 2 hours. The reaction medium is poured into water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30) to give 32.6 g (70%) of the expected product in the form of a white powder.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluted with a mixture of heptane and ethyl acetate (70/30)

Sources & evidence

ORD record
ord-026f7ecbce5d473c9a84f4e1801011ba
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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