Formic Acid → (S)-4-bromo-5-trifluoromethyl-indan-1-ol

HRID 471460Notes

Reaction equation

HRID 471460 reaction equation
C(N(CC)CC)C.C(O)=O.[Br:11][C:12]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C:16]2=[O:25].O>ClCCl>[Br:11][C:12]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C@@H:16]2[OH:25]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 867007731H-Inden-1-one, 4-bromo-2,3-dihydro-5-(trifluoromethyl)-

Product 1

HCID 86700775(S)-4-bromo-5-trifluoromethyl-indan-1-olYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (3.16 mL, 22.5 mmol) is dissolved in dichloromethane (40 mL) and cooled to 0° C. then formic acid (1.0 mL, 26.46 mmol) is added dropwise with cooling. After 20 minutes stirring 4-Bromo-5-trifluoromethyl-indan-1-one (2.1 g, 7.53 mmol) is added followed by Chloro([(1S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)-(mesitylene)ruthenium(II) complex (220 mg, 0.35 mmol) and the mixture is stirred overnight under argon at room temperature. Water is added, the mixture shaken and the phases separated. The organic phase is dried and concentrated under vacuum. The residue is purified by flash chromatography (0-15% ethyl acetate in cyclohexane) to give the title compound (yield 2.0 g).

Workup

  1. temperaturewith cooling
  2. additionis added
  3. stirringthe mixture shaken
  4. customthe phases separated
  5. customThe organic phase is dried
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by flash chromatography (0-15% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-5c2d5c7caba04d2c8224c5ad9afedb85
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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