Sodium borohydride → alpha-(Chloromethyl)-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-methanol

HRID 1108158Notes

Reaction equation

HRID 1108158 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH:18]([F:20])[F:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>C1COCC1>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH:18]([F:20])[F:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 187864052-Chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethanone

Product 1

HCID 18786418alpha-(Chloromethyl)-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
7.5 °C

Procedure

A mixture of 3.0 g of 2-chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethanone, 15 mL of THF, and 2 mL of pH 7 buffer was cooled to 5-10° C. 160 mg of NaBH4 was added, and stirring was continued for 1 h. The mixture was concentrated and triturated with water, filtered, and the solids were washed with hexane and dried in vacuo to afford 2.4 g (80%) of product, m.p. 66-68° C. 1H-NMR(CDCl3): δ2.82 (d, 1H, OH), 3.7 (ddd, 2H), 4.95 (m, 1H), 6.85 (t, 1H, J=60 Hz), 7.5 (d of AB q, 2H), 7.6 (m, 6H).

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated with water
  3. filtrationfiltered
  4. washthe solids were washed with hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-533c322f0c004cf1b0df4420a419c5e7
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

Loading…