Carbon tetrabromide → HCID 22407359, compound

HRID 440579Notes

Reaction equation

HRID 440579 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:42]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][Br:42])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54431298HCID 54431298, compound

Product 1

HCID 22407359HCID 22407359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

28.6 g (0.1 mol) of 4-(α-ethoxycarbonyl-benzyloxy)benzyl alcohol are dissolved in 300 ml of dichloromethane and mixed with 31.6 g (0.12 mol) of triphenylphosphine. Whilst cooling with ice, a solution of 40.0 g (0.12 mol) of carbon tetrabromide in 100 ml of dichloromethane is added dropwise. The mixture is stirred for 30 minutes at ambient temperature and then concentrated by evaporation. The residue is purified over a silica gel column (particle size: 0.063-0.02 mm), using as eluant first petroleum ether and then mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1 and 8:2). The unified fractions are evaporated down in vacuo.

Workup

  1. temperatureWhilst cooling with ice
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified over a silica gel column (particle size: 0.063-0.02 mm)
  4. temperatureof increasing polarity (9:1 and 8:2)
  5. customThe unified fractions are evaporated down in vacuo

Sources & evidence

ORD record
ord-8d3c2d046611493898849adc4a0f529a
Source dataset
uspto-grants-1996_05
Patent number
US05519138

Reaction notes

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