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

HRID 2364856Notes

Reaction equation

HRID 2364856 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-5881965b546d430e8fd512201cb350f2
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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