Sodium 4-chlorobenzenesulfinate → HCID 59750856, compound

HRID 748816Notes

Reaction equation

HRID 748816 reaction equation
Br[CH2:2][C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[CH2:5][O:6][Si:7]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O-:37])=[O:36])=[CH:31][CH:30]=1.[Na+]>C(O)CC>[C:20]([Si:7]([O:6][CH2:5][C:4]1[CH:24]=[CH:25][CH:26]=[CH:27][C:3]=1[CH2:2][S:35]([C:32]1[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=1)(=[O:37])=[O:36])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:21])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 23664783Sodium 4-chlorobenzenesulfinateHCID 59750893(2-Bromomethylbenzyloxy)-t-butyldiphenylsilane

Product 1

HCID 59750856HCID 59750856, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

In propanol (20 ml) was dissolved (2-bromo methylbenzyloxy)-t-butyldiphenylsilane (3.10 g, 7.05 mmol), followed by the addition of sodium 4-chlorobenzenesulfinate (1.80 g, 9.06 mmol). At 90° C., the resulting mixture was stirred for 14 hours. After the reaction mixture was allowed to cool down, the residue obtained by concentrating the reaction mixture under reduced pressure was added with ethyl acetate. The resulting mixture was washed with water, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, whereby the title compound (3.90 g, quant.) was obtained as a white solid.

Workup

  1. temperatureto cool down
  2. customthe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. additionwas added with ethyl acetate
  5. washThe resulting mixture was washed with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure, whereby the title compound (3.90 g, quant.)
  9. customwas obtained as a white solid

Sources & evidence

ORD record
ord-8ddd642693504851933b7e7468e604cf
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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