Water → 6-Bromo-3-pyridinemethanol

HRID 1440458Notes

Reaction equation

HRID 1440458 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 2389326-Bromonicotinic acid

Product 1

HCID 64212496-Bromo-3-pyridinemethanolYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of 6-bromonicotinic acid (13.8 g, 0.068 mol), prepared according to Campbell, et al. Aust. J. Chem. 1971, 24, 277, in THF (20 mL) was added 1.0M BH3 in THF (204 mL, 0.204 mol). The mixture was stirred at room temperature for 3 h, recolled to 0° C., and saturated aqueous K2CO3 and water were added. The mixture was extracted with EtOAc, and the combined extracts were washed with water, dried (MgSO4), and concentrated to give a yellow oil. Purification by flash chromatography (2% MeOH/CH2Cl2) gave 7.5 g (59%) of a yellow solid, mp 49°-51° C.

Workup

  1. customprepared
  2. stirringThe mixture was stirred at room temperature for 3 h
  3. customrecolled to 0° C.
  4. extractionThe mixture was extracted with EtOAc
  5. washthe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customPurification by flash chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-58142dbb796a4bc5b06437fc47163418
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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