Methanol → 2-(5-Bromopyridin-3-yl)acetonitrile

HRID 445754Notes

Reaction equation

HRID 445754 reaction equation
O=S(Cl)Cl.[Br:5][C:6]1[CH:7]=[C:8]([CH2:12]O)[CH:9]=[N:10][CH:11]=1.[C-:14]#[N:15].[K+].CO>O>[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:14]#[N:15])[CH:9]=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 24386Thionyl ChlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To SOCl2 (26.7 ml) cooled with an ice-bath was added portionwise (5-bromo-pyridin-3-yl)-methanol (ABCR, Karlsruhe, Germany, 26.6 mmol). The RM was refluxed for 1 h then was cooled at 0° C. and quenched with diethyl ether. The resulting precipitate was filtered, washed with cooled diethyl ether and dried under vacuum at 50° C. The solid was mixed with potassium cyanide (64.5 mmol), MeOH (35 ml) and water (14 ml) and the RM was refluxed for 2 h. The RM was cooled, quenched with aqueous K2CO3 and extracted with diethyl ether (3×). The combined organic layers dried over Na2SO4, filtered and evaporated to give the title compound as a purple solid. (HPLC: tR 2.16 min (Method A); M+H=197, 199 MS-ES)

Workup

  1. temperatureThe RM was refluxed for 1 h
  2. customquenched with diethyl ether
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with cooled diethyl ether
  5. customdried under vacuum at 50° C
  6. temperaturethe RM was refluxed for 2 h
  7. temperatureThe RM was cooled
  8. customquenched with aqueous K2CO3
  9. extractionextracted with diethyl ether (3×)
  10. dry with materialThe combined organic layers dried over Na2SO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-8408880bb99745e88e38777895495a92
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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