Hydrochloric Acid → 3-(2-(tert-Butyldimethylsilyloxy)ethylthio)benzoic acid

HRID 446380Notes

Reaction equation

HRID 446380 reaction equation
Br[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[SH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[Si:5]([O:4][CH2:3][CH2:2][S:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 579893363-(2-(tert-Butyldimethylsilyloxy)ethylthio)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2-Bromoethoxy)(tert-butyl)dimethylsilane (1.48 mL) was added dropwise to a suspension of 3-mercaptobenzoic acid (1.07 g) and potassium carbonate (1.91 g) in DMF (15 mL). The resulting suspension was stirred for 2 h. The reaction was carefully acidified by dropwise addition of aqueous HCl (2M, 10 mL) and poured into water (100 mL). The resulting aqueous was extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear oil. Yield 2.8 g.

Workup

  1. extractionThe resulting aqueous was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organics were washed with brine (50 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-187407d2bfad43f797f3a438a0070552
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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