Acetone cardice → 2-(6-bromo-5-fluoro-1H-indol-1-yl)ethanol

HRID 331044Notes

Reaction equation

HRID 331044 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12](OC)=[O:13])=[CH:4][C:3]=1[F:16].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(=O)=O.CC(C)=O>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[F:16]

Participants

5

Reactant 3

HCID 18522661Acetone cardiceHCID 21226445Aluminium lithium hydrideHCID 71090281Methyl 2-(6-bromo-5-fluoro-1H-indol-1-yl)acetate

Product 1

HCID 710904052-(6-bromo-5-fluoro-1H-indol-1-yl)ethanolYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(6-bromo-5-fluoro-1H-indol-1-yl)acetate (D77) (10.2 g, 35.7 mmol) was dissolved up in 81 mL of THF and cooled in a cardice/acetone bath before the addition of LiAlH4 (2N in THF solution) (17.83 mL, 35.7 mmol). The reaction mixture was left to stir in the cardice/acetone bath for 30 mins. Whilst still in the bath the reaction mixture was quenched by the dropwise addition of saturated sodium sulfate aqueous solution. The solid formed was filtered off and washed with ethyl acetate. The filtrate was washed with brine. The organic layer was passed through a hydrophobic frit and concentrated to afford title compound (8.852 g). LCMS (A): m/z (M+H)+ 258/260, C10H9BrFNO requires 257/259 (acidic).

Workup

  1. waitThe reaction mixture was left
  2. customWhilst still in the bath the reaction mixture was quenched by the dropwise addition of saturated sodium sulfate aqueous solution
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with ethyl acetate
  6. washThe filtrate was washed with brine
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-94067bdb7f104c4787aaec2c082cac26
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

Loading…