Carbon tetrabromide → HCID 70053591, compound

HRID 583373Notes

Reaction equation

HRID 583373 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[C:6]([CH3:12])[C:5]=1[N:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(Br)(Br)(Br)[Br:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH2:10][Br:34])[CH:7]=[C:6]([CH3:12])[C:5]=1[N:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17866627HCID 17866627, compound

Product 1

HCID 70053591HCID 70053591, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 1.08 g (2.37 mmol) of the product of Example 278 and 983 mg (2.96 mmol) of carbon tetrabromide in 24 ml of dichloromethane was added 933 mg (3.55 mmol) of triphenyl phosphine. The resulting mixture was stirred for 15 min and then concentrated in vacu. The residue was chromatographed on silica gel using EtOAc:Hexane (1:6) as eluant to provide 1.1 g (96%) of the desired product as a white crystalline solid. Electrospray Mass Spec 520 (M+H).

Workup

  1. concentrationconcentrated in vacu
  2. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1f790c00800d4a74b12dec7e019ee309
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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