Carbon tetrabromide → CBr4 triphenylphosphine

HRID 453250Notes

Reaction equation

HRID 453250 reaction equation
C(OC([C@@H](N1C(=O)CC(C=O)C1)CC)=O)(C)(C)C.[C:19]([Br:23])([Br:22])([Br:21])[Br:20].[C:24]1([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH:40]1[CH:39]=[CH:38][C:37]([P:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:42][CH:41]=1.[C:19]([Br:23])([Br:22])([Br:21])[Br:20]

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 183461161-[(1S)-1-(tertbutoxycarbonyl)propyl]-5-oxo-3-pyrrolidinecaboxaldehyde

Product 1

HCID 11387777CBr4 triphenylphosphine

Procedure

Alternatively to §6.2.3., halovinyl derivatives can be obtained by Wittig olefination of the 1-[(1S)-1-(tertbutoxycarbonyl)propyl]-5-oxo-3-pyrrolidinecarboxaldehyde 396 in the presence of a phosphine and an halogenomethane. For example, (2S)-2-(2-oxo-4-(2,2-dibromovinyl)-1-pyrrolidinyl)butanoic acid 2,2-(dimethyl)ethyl ester is obtained from aldehyde 396 and CBr4 in the presence of triphenylphosphine.

Sources & evidence

ORD record
ord-03b88f3cd62147c38495b8a836e4da45
Source dataset
uspto-grants-2013_07
Patent number
US08492416B2

Reaction notes

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