Sodium borohydride → HCID 58762592, compound

HRID 858704Notes

Reaction equation

HRID 858704 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:12])[CH:3]=1.[BH4-].[Na+]>CO.C(OCC)C>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 575272884-broMo-2-fluoro-5-Methoxy-benzaldehyde

Product 1

HCID 58762592HCID 58762592, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-Bromo-2-fluoro-5-methoxy-benzaldehyde (4.03 g, 17.33 mmol) from step (1) below in Methanol at 0° C. was added NaBH4 (0.65 g, 17.33 mmol). After the reaction mixture was stirred at 0° C. for 2 hours, it was allowed to warm to room temperature. The organic layer was taken up in ethyl ether, washed with water and dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (25–45% EtOAc in hexanes) to give the product. Yield: 3.90 g, 99.0%. 1H NMR (CDCl3) δ: 3.90 (s, 3H), 4.74 (d, J=6.02 Hz, 2H), 6.82 (d, J=6.1 Hz, 1H), 7.29 (d, J=10.58 Hz, 1H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (25–45% EtOAc in hexanes)
  7. customto give the product

Sources & evidence

ORD record
ord-0631f7cff48c4904950a90e079715060
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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