Acetyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indol-5-yl acetate

HRID 2423170Notes

Reaction equation

HRID 2423170 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1>[C:28]([O:18][C:17]1[C:9]([Br:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH:12]=[CH:11]2)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 672423064-Bromo-1-(phenylsulfonyl)-1H-indol-5-ol2×

Product 1

HCID 672413314-Bromo-1-(phenylsulfonyl)-1H-indol-5-yl acetateYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.29 g, 2.8 mmol) was added to a solution of 4-bromo-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 21, 0.67 g, 1.9 mmol) and acetyl chloride (0.22 g, 2.8 mmol) in THF (10 mL). The mixture was stirred for 10 minutes at room temperature and evaporated. The residue was partitioned between DCM and saturated aqueous NaHCO3. The reaction mixture was washed with saturated aqueous NaHCO3, and the organic phase was dried (MgSO4) and evaporated to give the title compound (0.6 g) as a red solid. MS m/z 394/396 [M+H]+.

Workup

  1. customevaporated
  2. customThe residue was partitioned between DCM and saturated aqueous NaHCO3
  3. washThe reaction mixture was washed with saturated aqueous NaHCO3
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ec6df60796c24876af7a0efac1d59ebd
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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