Methanol → (5-Bromo-3-pyridinyl)methanol

HRID 2113633Notes

Reaction equation

HRID 2113633 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[BH4-].[Na+].CO.O>C(O)(C)(C)C>[Br:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

1.1 1.3 g of ethyl 5-bromonicotinate are initially introduced in 40 ml of tert-butanol, and 427 mg of sodium borohydride are added. The entire mixture is heated under reflux (100° C.) and under N2 for one hour. 6 ml of methanol are then added. The mixture is stirred overnight. 10 ml of water is added to the reaction solution. The mixture is then extracted with dichloromethane, dried using sodium sulfate and evaporated in a rotary evaporator, giving 300 mg of (5-bromopyridin-3-yl)methanol.

Workup

  1. temperatureThe entire mixture is heated
  2. extractionThe mixture is then extracted with dichloromethane
  3. customdried
  4. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-87210240e42b4d9fb76e0e0e05f97748
Source dataset
uspto-grants-2008_10
Patent number
US07432282B2

Reaction notes

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