Sodium borohydride → HCID 58762592, compound

HRID 1453155Notes

Reaction equation

HRID 1453155 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-c03338deefc14272b987c302f7d1bd75
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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