Carbon tetrabromide → HCID 21476913, compound

HRID 2293583Notes

Reaction equation

HRID 2293583 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21476897HCID 21476897, compound

Product 1

HCID 21476913HCID 21476913, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 0.405 g (1.94 mmol) of the product of Step D dissolved in 5.0 mL of methylene chloride was added 0.638 g (2.43 mmol) of triphenylphosphine followed by 0.806 g (2.43 mmol) of carbon tetrabromide at room temperature. The reaction mixture was stirred for 30 minutes at room temperature, then the magnetic stir bar was removed and the methylene chloride was evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 10% EtOAc-hexane, and evaporation of the purified fractions and solvent removal in vacuo afforded 0.496 g (94%) of the title compound.

Workup

  1. customthe magnetic stir bar was removed
  2. customthe methylene chloride was evaporated in vacuo
  3. customThe residue was purified on a silica gel flash chromatography column
  4. washeluted with 10% EtOAc-hexane, and evaporation of the purified fractions and solvent removal in vacuo

Sources & evidence

ORD record
ord-1c48d9c1d6c946cda3fe851aca13b0e9
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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