3-Bromo-4-fluorobenzyl Bromide → (S)-N-((2S,3S)-1-(3-Bromo-4-fluorophenyl)-3,4-bis(tert-butyldimethylsilyloxy)butan-2-yl)-2-methylpropane-2-sulfinamide

HRID 20066

Reaction equation

HRID 20066 reaction equation
[Si:1]([O:8][C@H:9]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])/[CH:10]=[N:11]/[S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:27][C:28]1[CH:33]=[C:32]([CH2:34]Br)[CH:31]=[CH:30][C:29]=1[F:36]>>[Br:27][C:28]1[CH:33]=[C:32]([CH2:34][C@H:10]([NH:11][S@:12]([C:14]([CH3:15])([CH3:16])[CH3:17])=[O:13])[C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH:31]=[CH:30][C:29]=1[F:36]

Participants

3

Reactant 2

HCID 129227103-Bromo-4-fluorobenzyl BromideHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 67304989(S)-N-((2S,3S)-1-(3-Bromo-4-fluorophenyl)-3,4-bis(tert-butyldimethylsilyloxy)butan-2-yl)-2-methylpropane-2-sulfinamide

Procedure

The title compound was prepared from (S,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide and 2-bromo-4-(bromomethyl)-1-fluorobenzene using a method analogous to that described in Examples 509 and 510.

Sources & evidence

ORD record
ord-de5afd8195a94c1e80d9d1d910874574
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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