Methanol → [4-(Phenylsulfonyl)phenyl]methanol

HRID 2376966Notes

Reaction equation

HRID 2376966 reaction equation
[C:1]1([S:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[BH4-].[Na+].O>O1CCCC1>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:14][OH:15])=[CH:16][CH:17]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 144174774-(Benzenesulfonyl)benzaldehyde

Product 1

HCID 12801750[4-(Phenylsulfonyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Phenylsulfonyl)benzaldehyde (prepared according to the method of Ulman et al., J. Org. Chem. (1989), 54(19), 4691-2; 12.3 g, 50 mmol) was dissolved in tetrahydrofuran and methanol was added, followed by careful addition of sodium borohydride (2.0 g, 52.9 mmol). The reaction was stirred for 1 hour before pouring into water and extracting with ethyl acetate. The organic layer was dried over MgSO4 and evaporated in vacuo to give [4-(phenylsulfonyl)phenyl]methanol. This was treated with phosphorus tribromide and heated to reflux for 16 hours. The cooled reaction mixture was poured onto ice and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with dichloromethane, to give 1-(bromomethyl)-4-(phenylsulfonyl)benzene (10.1 g, 65%). δH (500 MHz, CDCl3): 7.96-7.90 (4H, m), 7.59-7.56 (1H, m), 7.52-7.49 (4H, m).

Workup

  1. extractionextracting with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c8733a26c7b744e8b73f3b578d14ac40
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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