Carbon tetrabromide → HCID 57519121, compound

HRID 1785362Notes

Reaction equation

HRID 1785362 reaction equation
[CH3:1][N:2]([CH3:36])[C:3](=[O:35])[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:32])[CH2:12][CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([CH:33]=[CH2:34])[CH:6]=1.C(Br)(Br)(Br)[Br:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:36][N:2]([CH3:1])[C:3](=[O:35])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([Br:38])([OH:32])[CH2:12][CH2:13][O:14][Si:15]([C:28]([CH3:29])([CH3:30])[CH3:31])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([CH:33]=[CH2:34])[CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57519120HCID 57519120, compound

Product 1

HCID 57519121HCID 57519121, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (3.00 g, 5.95 mmol) synthesized in step (f) of Example 192 and carbon tetrabromide (3.98 g, 12.0 mmol) in dichloromethane (20 ml) was added triphenyl phosphine (3.14 g, 12.0 mmol) at room temperature, and the resulting mixture was stirred for 1 hour at room temperature under a nitrogen atmosphere. After stirring, the reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1-2:1) as the eluent to afford the title compound (2.62 g, yield: 78%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. customthe reaction mixture was evaporated in vacuo
  3. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-294bb25f02364fc6a9729d57a284d748
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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