Water → (5-Bromo-2-chloropyridin-3-yl)methanol

HRID 515805Notes

Reaction equation

HRID 515805 reaction equation
[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].[Br:6][C:7]1[CH:8]=[N:9][C:10]([Cl:17])=[C:11]([CH:16]=1)[C:12](OC)=[O:13].O>C(Cl)Cl>[Br:6][C:7]1[CH:16]=[C:11]([CH2:12][OH:13])[C:10]([Cl:17])=[N:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2763343Methyl 5-bromo-2-chloronicotinateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 23091039(5-Bromo-2-chloropyridin-3-yl)methanolYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of NaBH4 (5.8 g, 152.6 mmol, 4 eq) and anhydrous CaCl2 (16.9 g, 152.6 mmol) in dry DCM (100 mL) at 0° C., was added slowly methyl 5-bromo-2-chloronicotinate (9.5 g, 38.15 mmol). The resulting mixture was stirred at room temperature for 12 h. Water was added to the reaction mixture at 0° C. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo, to afford 6.8 g (crude) of (5-bromo-2-chloropyridin-3-yl)methanol, which was used in the next step without further purification. LCMS [M+H]+ 223.1.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58a6e66ec3a34b90b451b05c0d071def
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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