6-bromo-1H-indole-2-carboxylic acid → (6-Bromo-1H-indol-2-yl)methanol

HRID 2365415Notes

Reaction equation

HRID 2365415 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11](O)=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][OH:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 40116966-bromo-1H-indole-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13567957(6-Bromo-1H-indol-2-yl)methanolYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH4 (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0° C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15% aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3×). The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

Workup

  1. customThe reaction was quenched with water and 15% aqueous NaOH at 0° C.
  2. customto form a precipitate which
  3. filtrationwas filtered through Celite
  4. extractionThe filtrate was extracted with EtOAc (3×)
  5. dry with materialThe extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70568d71d38f4d43b810e4567dbe67d6
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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