(2-Bromoethoxy)-tert-butyldimethylsilane → 2-(4-Bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

HRID 220166Notes

Reaction equation

HRID 220166 reaction equation
Br[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[CH3:13].CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:12]([O:14][C:15](=[O:24])[CH:16]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6])[CH3:13]

Participants

5

Reactant 3

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane2×HCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 592383032-(4-Bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester (XXXI) is prepared by alkylation of the corresponding potassium enolate with XXX. The reaction is typically carried out by deprotonating (4-bromo-phenyl)-acetic acid ethyl ester with potassium tert-butoxide in dimethylformamide at room temperature for one hour, then cooling the reaction to zero degrees Celsius and slowly adding XXX, followed by stirring at room temperature for twelve hours.

Workup

  1. customat room temperature
  2. customfor one hour
  3. temperaturecooling
  4. customthe reaction to zero degrees Celsius

Sources & evidence

ORD record
ord-bb2fcee14b8e4bcdba253e89485a65b3
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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