Carbon tetrabromide → HCID 86761085, compound

HRID 644573Notes

Reaction equation

HRID 644573 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Si:25]([O:32][C:33]1[CH:34]=[C:35](/[C:39](/[CH2:43][CH3:44])=[CH:40]/[CH:41]=O)[CH:36]=[CH:37][CH:38]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>ClCCl.[Zn]>[C:28]([Si:25]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](/[C:39](/[CH2:43][CH3:44])=[CH:40]/[CH:41]=[C:20]([Br:24])[Br:21])[CH:34]=1)([CH3:27])[CH3:26])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86761084HCID 86761084, compound

Product 1

HCID 86761085HCID 86761085, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1.17 g (18 mmol) of zinc powder, 4.7 g (18 mmol) of triphenylphosphine and 5.9 g (18 mmol) of carbon tetrabromide are stirred for 45 minutes in 150 ml of dichloromethane. A solution of 2.6 g (9 mmol) of (E)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]pent-2-en-1-al in 10 ml of dichloromethane is added drop by drop. The reaction medium is stirred for 1 hour, then extracted with a mixture of water and of dichloro-methane. The residue is filtered on a silica column (eluent dichloromethane). A yellow oil is obtained (m=3.3 g; Y=83%).

Workup

  1. extractionextracted with a mixture of water and of dichloro-methane
  2. filtrationThe residue is filtered on a silica column (eluent dichloromethane)
  3. customA yellow oil is obtained (m=3.3 g; Y=83%)

Sources & evidence

ORD record
ord-b338b375931c498db3ae966ea4b4e077
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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