Thiophenol → 2-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine

HRID 741819Notes

Reaction equation

HRID 741819 reaction equation
[C:1]1(S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])(C)[CH3:9].[Br:16][C:17]1[N:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[CH:19][CH:18]=1.Br[C:27]1[CH:28]=[C:29](O)C=[CH:31][CH:32]=1>>[Br:16][C:17]1[N:22]=[C:21]([CH2:23][O:25][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([C:9]2[CH:29]=[CH:28][CH:27]=[CH:32][CH:31]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 7969ThiophenolHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 233702372-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine

Procedure

Following the procedure described for Phenol 7, Step 1 but substituting tert-butyldiphenylsilyl chloride for tert-butyldimethylsilyl chloride and 6-bromopyridin-2-methanol from Step 1 for 3-bromophenol, the title compound was obtained as a yellow oil.

Sources & evidence

ORD record
ord-949cbe8468a445e995697b78f7a65a66
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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