Borane → 2-(3-Iodophenyl)ethanol

HRID 1179645Notes

Reaction equation

HRID 1179645 reaction equation
B.[I:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](O)=[O:11])[CH:6]=[CH:7][CH:8]=1.[Cl-].[NH4+]>C1COCC1>[I:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 25517Ammonium ChlorideHCID 38702203-Iodophenylacetic acid

Product 1

HCID 151698502-(3-Iodophenyl)ethanolYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane (1M, THF, 2.5 eq., 38.2 mL) was added dropwise to a stirred solution of (3-iodophenyl)acetic acid (4.0 g) in THF (100 mL) cooled to 0□C. The resulting mixture was stirred at 0 □C for 1 h then warmed to room temperature and stirred for a further 3 h. The mixture was poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated. The crude was purified by column chromatography (SPE cartridge, SiO2), using cyclohexane-ethyl acetate (70:30) as eluent to afford the title compound (3.5 g, 92% yield).

Workup

  1. temperaturecooled to 0□C
  2. stirringstirred for a further 3 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography (SPE cartridge, SiO2)

Sources & evidence

ORD record
ord-ca131ef886a245599fb994c5084e12ff
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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