Sodium borohydride → HCID 58687965, compound

HRID 746417Notes

Reaction equation

HRID 746417 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[N:8][C:7]([C:12]([F:15])([F:14])[F:13])=[C:6]([Br:16])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[N:8][C:7]([C:12]([F:15])([F:14])[F:13])=[C:6]([Br:16])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 534038503,5-Dibromo-2-methoxy-6-(trifluoromethyl)pyridine-4-carbaldehyde

Product 1

HCID 58687965HCID 58687965, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3,5-dibromo-2-methoxy-6-(trifluoromethyl)isonicotinaldehyde (980 mg, 2.7 mmol) in ethanol (10 mL), was added sodium borohydride (102 mg, 2.7 mmol). The reaction mixture was stirred for 20 min, concentrated, and the residue was purified by flash column (silica gel, 50% EtOAc/hexane) to yield [3,5-dibromo-2-methoxy-6-(trifluoromethyl)pyridin4-yl]methanol (717 mg, 72.8%). 1H-NMR (400 MHz, CDCl3) δ 5.10 (s, 2H), 4.05 (s, 3H), 2.32 (br s, 1H).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by flash column (silica gel, 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-f9b1d6b88a5d4e038f3082983fb404f9
Source dataset
uspto-grants-2008_07
Patent number
US07393844B2

Reaction notes

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