Carbon tetrabromide → HCID 5314571, compound

HRID 1372623Notes

Reaction equation

HRID 1372623 reaction equation
[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][Br:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11008492cis-4-Benzyloxy-2-buten-1-ol

Product 1

HCID 5314571HCID 5314571, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (Z)-4-benzyloxy-2-buten-1-ol (2.0 g, 11.2 mmol) in methylene chloride (40 ml) were added carbon tetrabromide (4.46 g, 13.4 mmol) and triphenylphosphine (3.51 g, 13.4 mmol) at 0° C. under stirring in a nitrogen gas stream. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from hexane/ethyl acetate (4/1) eluate fractions, the title compound (2.76 g, 100%) was obtained as a colorless oil.

Workup

  1. stirringAfter stirring at room temperature for 1.5 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from hexane/ethyl acetate (4/1) eluate fractions

Sources & evidence

ORD record
ord-7f73a23fb58f447cb9224399ae911677
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…