Boron trifluoride etherate → 2-(6-Bromopyridin-2-yl)ethanol

HRID 385856Notes

Reaction equation

HRID 385856 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1.[Cl-].[Na+].O.[Cl-].[NH4+].C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 468357142-(6-Bromopyridin-2-yl)acetic acid

Product 1

HCID 468357132-(6-Bromopyridin-2-yl)ethanol

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (6-bromopyridin-2-yl)acetic acid (1.1 g, 5.09 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C. Sodium borohydride (0.385 g, 10.18 mmol) was slowly added followed by the addition of boron trifluoride diethyl etherate (1.29 ml, 10.18 mmol). The reaction was allowed to come to room temperature. After 2 hrs, the reaction was diluted with brine, ammonium chloride and ethyl acetate. After layer separation, the organic layer was dried over sodium sulfate, filtered and concentrated. The crude residue was purification by silica gel chromatography (3:7 hexane:ethyl acetate) to yield the title compound.

Workup

  1. customto come to room temperature
  2. customAfter layer separation
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurification by silica gel chromatography (3:7 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-5309ad10efe947b99a9255effa789d14
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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