Carbon tetrabromide → HCID 54394913, compound

HRID 2121239Notes

Reaction equation

HRID 2121239 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([CH2:11]O)=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([CH2:11][Br:22])=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10571934HCID 10571934, compound

Product 1

HCID 54394913HCID 54394913, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a −10° C. solution in dichloromethane of the product of Example 319E (830 mg, 2.17 mmol) and carbon tetrabromide (864 mg, 2.60 mmol) was added triphenylphosphine (626 mg, 2.39 mmol) and the reaction mixture was warmed to 0° C. over 1 hour. The cold bath was then removed and stirring was continued for 2 hours. The reaction mixture was concentrated in vacuo and purified by chromatography on silica gel (5% ethyl acetate-hexanes) to give the desired compound (1.1 g) which also contained some triphenylphosphine.

Workup

  1. customThe cold bath was then removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by chromatography on silica gel (5% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-593df987bc3f45f890f87c71e3df2193
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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