Triethylamine → (2-Bromopyridin-4-yl)methanol

HRID 1434705Notes

Reaction equation

HRID 1434705 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12](O)=[O:13].ClC(OCC(C)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(O)(=O)C.C1COCC1>[Br:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][N:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 2227012-Bromoisonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14512957(2-Bromopyridin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

30.2 ml (295 mmol) of triethylamine is added to 56.5 g (280 mmol) of 2-bromo-isonicotinic acid in 1.21 of THF. Then, it is cooled to −10° C. and mixed drop by drop with 38.2 ml (295 mmol) of isobutyl chloroformate. After stirring has been continued for one hour at −10° C., it is cooled to −70° C. and mixed drop by drop with 590 ml (590 mmol) of LiAlH4 solution (1 M in THF). After stirring is continued for one hour at −70° C., it is allowed to reach −40° C. 600 ml of 50% acetic acid is added. It is stirred overnight at room temperature. The insoluble components are suctioned off, and the filtrate is concentrated by evaporation. The residue is purified on silica gel with hexane and hexane/ethyl acetate 1:1. 28.0 g of white solidifying oil accumulates.

Workup

  1. temperatureit is cooled to −70° C.
  2. stirringAfter stirring
  3. waitis continued for one hour at −70° C.
  4. customto reach −40° C
  5. stirringIt is stirred overnight at room temperature
  6. concentrationthe filtrate is concentrated by evaporation
  7. customThe residue is purified on silica gel with hexane and hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-fa764d82aed84020af5c62ff621cef76
Source dataset
uspto-grants-2009_11
Patent number
US07615565B2

Reaction notes

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