Methanol → HCID 21886104, compound

HRID 2216006Notes

Reaction equation

HRID 2216006 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+].C[CH2:14][O:15]C(C)=O.[CH3:19]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]([O:15][CH3:14])[O:8][CH3:19])[CH:9]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 728635-BromosalicylaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21886104HCID 21886104, compound

Procedure

To a solution of 5-bromo-2-hydroxy-benzaldehyde (1 g, 4.9 mmol, Aldrich Chemical Company) in MeOH (25 mL) at 0° C., sodium borohydride (226 mg, 5.9 mmol) was added slowly with stirring. After the addition, the reaction was allowed to warm to rt and stir for an additional hour. Reaction mixture was dissolved into EtOAc and washed with brine (20 mL×2). The organic layer was dried over sodium sulfate. Removal of the solvents in vacuo gave the title compound (1.2 g, quantitative) a yellow oil which was used with out further purification. 1H-NMR (CD3OD): δ 7.35 (m, 2H), 6.75–6.77 (d, 1H, J=7.2 Hz), 5.55 (s, 1H), 3.33 (s, 6H).

Workup

  1. additionAfter the addition
  2. stirringstir for an additional hour
  3. customReaction mixture
  4. washwashed with brine (20 mL×2)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-f7ac69682d204a44831e781297f0bd5b
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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