Carbon tetrabromide → HCID 87504008, compound

HRID 644578Notes

Reaction equation

HRID 644578 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH2:37][CH3:38])=[CH:34]/[CH:35]=O)[CH:30]=[CH:31][CH:32]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:58](Br)(Br)([Br:60])[Br:59]>[Zn]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH2:37][CH3:38])=[CH:34]/[CH:35]=[C:58]([Br:60])[Br:59])[CH:30]=[CH:31][CH:32]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:22])[CH3:23])([CH3:19])[CH3:20])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 87503811HCID 87503811, compound

Product 1

HCID 87504008HCID 87504008, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In a manner analogous to example 2g, by reaction of 9 g (16.3 mmol) of (E)-3-(3-{2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)-phenyl]ethyl}phenyl)pent-2-enal (prepared in example 1j) with 2.1 g (32.5 mmol) of zinc powder, 8.5 g (32.5 mmol) of triphenylphosphine and 108 g (32.5 mmol) of carbon tetrabromide. A yellow oil is obtained (m=11.3 g; Y=98%).

Workup

  1. customA yellow oil is obtained (m=11.3 g; Y=98%)

Sources & evidence

ORD record
ord-4947f10519df4e1e9199626dde4a836b
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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