6-Bromopyridine-2-carbaldehyde → (6-Bromopyridin-2-yl)methanol

HRID 877000Notes

Reaction equation

HRID 877000 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 3517811(6-Bromopyridin-2-yl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-bromopyridine-2-carbaldehyde (10.00 g, 53.76 mmol) in MeOH (120 mL) was treated with sodium borohydride (2.04 g, 53.76 mmol), stirred for 1 h and partitioned between EtOAc and water. The organic phase was separated and the aqueous re-extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (9.76 g, 97%) as a pale-yellow liquid; LC-MS retention time 1.52 min, (M+H)+ 188 and 190.

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic phase was separated
  3. extractionthe aqueous re-extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b91276a3a88747e29347f7e94872cac1
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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