Chloroacetyl chloride → HCID 86691666, compound

HRID 85091Notes

Reaction equation

HRID 85091 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([CH3:15])[NH:12][C:9]2=[N:10][CH:11]=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:18](=[O:19])[CH2:17][Cl:16])=[C:13]([CH3:15])[NH:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 454896915-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 86691666HCID 86691666, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (1.57 g, 11.84 mmol) in dichloromethane (50 mL) was added 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine. After stirring for 30 min, chloroacetyl chloride (1.33 g, 11.84 mmol) was added and the reaction mixture was stirred for 2 hours at room temperature. On completion, solvents were evaporated and quenched with aq. NaHCO3 solution at 0° C. Resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered through a plug of silica gel. Solvent was evaporated to dryness to give 1-(5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-chloro-ethanone (0.650 g, 95% yield).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. customOn completion, solvents were evaporated
  3. customquenched with aq. NaHCO3 solution at 0° C
  4. customResulting mixture
  5. extractionwas extracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated to dryness

Sources & evidence

ORD record
ord-d73147c946b9437fbb94cd2fa37ea539
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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