Sodium borohydride → 2-(4-Bromo-2-fluorophenyl)-2-methylpropan-1-ol

HRID 858636Notes

Reaction equation

HRID 858636 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[C:4]([F:13])[CH:3]=1.[BH4-].[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:12])[CH2:9][OH:10])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 587625612-(4-Bromo-2-fluorophenyl)-2-methylpropanal

Product 1

HCID 587623442-(4-Bromo-2-fluorophenyl)-2-methylpropan-1-olYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-Bromo-2-fluoro-phenyl)-2-methyl-propionaldehyde (1.37 g, 5.58 mmol) in MeOH (18 ml) at 0° C. was added NaBH4 (0.21 g, 5.58 mmol). After being stirred for 2 hours at 0° C., the mixture was allowed to warm to room temperature. The reaction mixture was diluted with water (20 ml) and extracted with ether (3×75 ml). The combined organic layers were dried over MgSO4. The solvent was removed, and the residue was purified by flash column chromatography (15–35% EtOAc in Hexane) to give the product (1.10 g, 80.0% yield). 1H NMR (CDCl3) δ: 1.23 (s, 1 H) 1.35 (s, 3 H) 1.35 (s, 3 H) 3.75 (d, J=1.26 Hz, 2 H) 7.17 (d, J=2.27 Hz, 1 H) 7.20 (d, J=3.03 Hz, 1 H) 7.22 (m, 1 H).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ether (3×75 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customThe solvent was removed
  5. customthe residue was purified by flash column chromatography (15–35% EtOAc in Hexane)

Sources & evidence

ORD record
ord-1454bc10190947fc8b8e997f8e984ce5
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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