Sodium borohydride → HCID 69353261, compound

HRID 1349940Notes

Reaction equation

HRID 1349940 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([N+:14]([O-:16])=[O:15])[C:7]([O:12][CH3:13])=[C:8]([CH:11]=1)[CH:9]=[O:10]>CO.O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]([N+:14]([O-:16])=[O:15])[C:7]([O:12][CH3:13])=[C:8]([CH:11]=1)[CH2:9][OH:10]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 210937475-Bromo-2-methoxy-3-nitrobenzaldehyde

Product 1

HCID 69353261HCID 69353261, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (4 g) was added in portions to a stirring solution of crude 5-bromo-2-methoxy-3-nitrobenzaldehyde (20.5 g) in methanol (350 mL) and tetrahydrofuran (150 mL) at 0° C. After 1 h, the methanol was removed in vacuo. The residue was treated with cold water (150 mL) and extracted with diethyl ether (2×150 mL). The combined organic layer was evaporated in vacuo to give a crude oil. Silica gel chromatography eluting with ethyl acetate in petroleum ether (10–40%) gave the title compound (17 g) as a solid.

Workup

  1. customthe methanol was removed in vacuo
  2. additionThe residue was treated with cold water (150 mL)
  3. extractionextracted with diethyl ether (2×150 mL)
  4. customThe combined organic layer was evaporated in vacuo
  5. customto give a crude oil
  6. washSilica gel chromatography eluting with ethyl acetate in petroleum ether (10–40%)

Sources & evidence

ORD record
ord-1f72f1a800ac48aeb6e9e41e2e9b490f
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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