Benzoyl chloride → HCID 10900174, compound

HRID 411971Notes

Reaction equation

HRID 411971 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([Li])(C)(C)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:23])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 249055-BromoindoleHCID 178418306HCID 178418306, compound

Product 1

HCID 10900174HCID 10900174, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromoindole(1.0 g, 5.10 mmol) was dissolved in THF (10 mL) and the resulting solution was cooled to −78° C. t-Butyl lithium (1.7 M in pentane, 10.5 mL, 17.9 mmol) was added dropwise and the solution stirred for 30 minutes before being added to a solution of benzoyl chloride (0.86 g, 6.12 mmol) in THF (10 mL) at −78° C. via cannula. The reaction mixture was allowed to warm to room temperature and was stirred overnight and was then quenched with saturated ammonium chloride and diluted with ethyl acetate. The organic phase was washed with water and brine, dried (Na2SO4), filtered and concentrated. Silica gel chromatography using 20% hexane in ethyl acetate as the eluent provided the title compound as a beige solid (0.40 g, 35%).

Workup

  1. additionwas added dropwise
  2. stirringwas stirred overnight
  3. customwas then quenched with saturated ammonium chloride
  4. additiondiluted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9e22afc3b7c845f0a5bdc7e7483f589d
Source dataset
uspto-grants-2003_05
Patent number
US06562809B1

Reaction notes

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