1-(4-bromophenyl)-2-{[2-(4-bromophenyl)-2-oxoethyl]thio}ethan-1-one → 2,2'-Sulfanediylbis[1-(4-bromophenyl)ethan-1-ol]

HRID 1471017Notes

Reaction equation

HRID 1471017 reaction equation
[S:1]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=[O:14])[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>C(O)C>[S:1]([CH2:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=1)[OH:4])[CH2:12][CH:13]([C:15]1[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=1)[OH:14]

Participants

4

Reactant 2

HCID 2900341-(4-bromophenyl)-2-{[2-(4-bromophenyl)-2-oxoethyl]thio}ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 573460262,2'-Sulfanediylbis[1-(4-bromophenyl)ethan-1-ol]

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 159A (5.0 g, 11.68 mmol) in ethanol (78 mL) was added sodium borohydride (0.972 g, 25.7 mmol) portionwise and the mixture was stirred at room temperature for 20 minutes. Afterwards the solution was concentrated, then a solution of 1N aqueous hydrochloric acid (100 mL) was added and extracted with EtOAc. The organic extract was dried, filtered and concentrated to 5.05 g (100%) of a colorless solid as the title compound.

Workup

  1. concentrationAfterwards the solution was concentrated
  2. additiona solution of 1N aqueous hydrochloric acid (100 mL) was added
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. customwas dried
  6. filtrationfiltered
  7. concentrationconcentrated to 5.05 g (100%) of a colorless solid as the title compound

Sources & evidence

ORD record
ord-3b401bdeb9284ee8b49002bc19e28763
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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