Ethyl 5-bromopyridine-3-carboxylate → (5-Bromo-3-pyridinyl)methanol

HRID 656509Notes

Reaction equation

HRID 656509 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[N:7][CH:6]=1)C.[BH4-].[Na+]>CO>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of ethyl-5-bromonicotinate (1.0 g, 4.3 mmoL) in MeOH (15 mL) was added sodium borohydride (650 mg, 17 mmol) portion wise. After 30 min. the reaction was quenched by the addition of water (10 mL). The reaction was then extracted with methylene chloride (3×). The extracts were combined, dried (MgSO4) the filtrate was concentrated and purified by column chromatography on silica gel (0 to 80% ethyl acetate/hexanes) to produce 475 mg (60%) as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 8.49 (s, 1H), 7.91 (s, 1H), 4.73 (s, 2H), 2.51 (s, br, 1H). Mass spec.: 188.12 (MH)+.

Workup

  1. customAfter 30 min. the reaction was quenched by the addition of water (10 mL)
  2. extractionThe reaction was then extracted with methylene chloride (3×)
  3. dry with materialdried (MgSO4) the filtrate
  4. concentrationwas concentrated
  5. custompurified by column chromatography on silica gel (0 to 80% ethyl acetate/hexanes)
  6. customto produce 475 mg (60%) as a clear oil

Sources & evidence

ORD record
ord-9e780f32c3384d53841f9853632bdb5b
Source dataset
uspto-grants-2011_12
Patent number
US08071778B2

Reaction notes

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