Sodium borohydride → (3,5-Difluoro-4-(methylthio)phenyl)methanol

HRID 1468831Notes

Reaction equation

HRID 1468831 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:14])[C:11]=1[S:12][CH3:13])[CH:7]=[O:8]>CO.C(Cl)Cl>[F:14][C:10]1[CH:9]=[C:6]([CH2:7][OH:8])[CH:5]=[C:4]([F:3])[C:11]=1[S:12][CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 227466823,5-Difluoro-4-(methylthio)benzaldehyde

Product 1

HCID 22746033(3,5-Difluoro-4-(methylthio)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (25 mg, 0.66 mmol) was added to a 0° C. slurry of the product of step A (124 mg, 0.659 mmol) in methanol (4.39 mL). After 30 min the reaction mixture was warmed to room temperature, and at 1.5 h the reaction was diluted with DCM and quenched with 0.1 N HCl. The aqueous was extracted with DCM (2×) and then washed with saturated aqueous NaCl (1×). The combined organic layer was dried over Na2SO4, filtered and evaporated in vacuo to yield the title compound. 1H NMR (500 MHz, CDCl3) δ 6.81 (d, J 7.5 Hz, 2H), 4.55 (s, 2H), 3.23 (s, 1H), 2.37 (s, 3H).

Workup

  1. customquenched with 0.1 N HCl
  2. extractionThe aqueous was extracted with DCM (2×)
  3. washwashed with saturated aqueous NaCl (1×)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a639cd90cef487a8bfac44a70a43645
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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