Carbon tetrabromide → HCID 19385699, compound

HRID 2255587Notes

Reaction equation

HRID 2255587 reaction equation
O[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([O:21][CH3:22])[CH:4]=1.C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:24][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([O:21][CH3:22])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19385726HCID 19385726, compound

Product 1

HCID 19385699HCID 19385699, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 0.490 g (1.62 mmol) of the product of Step A dissolved in 8 mL of CH2Cl2 was added 0.673 g (2.03 mmol) of carbon tetrabromide and 0.531 g (2.03 mmol) of triphenylphosphine. The reaction mixture was stirred for 1.5 hours and was allowed to slowly warm to room temperature. The reaction mixture was then concentrated in vacuo, and purified on a silica gel flash chromatography column eluted with 15% ethyl acetate/hexane to afford 0.478 g (81%) of the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified on a silica gel flash chromatography column
  3. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9b09b9b62213439eab0d13d526099e45
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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