Sodium borohydride → HCID 21099499, compound

HRID 2376958Notes

Reaction equation

HRID 2376958 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21099498HCID 21099498, compound

Product 1

HCID 21099499HCID 21099499, compoundYield 133.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[(2-bromophenyl)thio]benzaldehyde (Step 1, 5 g, 12.7 mmol) in ethanol under nitrogen (63 mL) was added sodium borohydride (5.7 g, 127.2 mmol). The reaction was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to yield {4-[(2-bromophenyl)thio]phenyl}methanol as a colourless oil (5.0 g, 99%). δH (400 MHz, d6 DMSO): 7.65-7.60 (1H, m), 7.41 (4H, s), 7.27-7.21 (1H, m), 7.14-7.08 (1H, m), 6.83 (1H, dd, J=1.4, 7.9 Hz), 5.32-5.28 (1H, m), 4.56-4.53 (2H, m).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-ea0be36349d24ed082bc270c27a3be31
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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