Ammonium Chloride → (6-Bromo-2-chloropyridin-3-yl)methanol

HRID 595774Notes

Reaction equation

HRID 595774 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([Cl:10])[N:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.CO>[Br:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]([CH2:6][OH:7])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 455881966-Bromo-2-chloropyridine-3-carbaldehyde

Product 1

HCID 70701001(6-Bromo-2-chloropyridin-3-yl)methanolYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-bromo-2-chloronicotinaldehyde (5.40 g, 24.50 mmol) in THF (30 ml) and MeOH (10.0 ml) at 0° C. was added NaBH4 (0.927 g, 24.50 mmol). The mixture was stirred at 0° C. for 2 h. Saturated NH4Cl (50 ml) was added and the mixture extracted with ethyl acetate, dried over (Na2SO4), filtered and concentrated in vacuo to give (6-bromo-2-chloropyridin-3-yl)methanol (5.50 mg, yield: 101%). MS (M+H)+: 224.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialdried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8be3375d4c234d3aa54baffbd5a15feb
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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