4-(Chloromethyl)benzoyl chloride → HCID 10502995, compound

HRID 375628Notes

Reaction equation

HRID 375628 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:16][N:17]([CH3:36])[C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH:27]=2)[CH:22]=[CH:21]1)=[O:19]>C(Cl)Cl>[CH3:16][N:17]([CH3:36])[C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH:27]=2)[C:22]([C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=2)=[CH:21]1)=[O:19]

Participants

5

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 18993299HCID 18993299, compound

Product 1

HCID 10502995HCID 10502995, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-(chloromethyl)benzoyl chloride (804 mg, 4.26 mmol) in CH2Cl2 (21 mL) was added AlCl3 (850 mg, 6.39 mmol) in a single portion, and the yellow solution was stirred for 15 min at ambient temperature. A solution of 6-(4-fluorophenyl)indole-1-carboxylic acid dimethylamide (1.00 g, 3.55 mmol), prepared as in step 1, in CH2Cl2 was added dropwise and the dark solution was stirred for 2 hours at ambient temperature. Additional AlCl3 (0.24 g, 1.78 mmol) was added and the reaction mixture was stirred for 0.5 hours. The reaction mixture was poured into a separatory funnel containing ice water and CH2Cl2. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and concentrated in vacuo. Pure 6-(4-fluorophenyl)-3-(4 -chloromethylbenzoyl)indole-1-carboxylic acid dimethylamide (294 mg) was obtained by chromatography on silica gel (25%, then 50% ethyl acetate/hexanes).

Workup

  1. stirringthe dark solution was stirred for 2 hours at ambient temperature
  2. stirringthe reaction mixture was stirred for 0.5 hours
  3. additionThe reaction mixture was poured into a separatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted three times with CH2Cl2
  6. washThe combined organic layers were washed with saturated aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-851e0c56a02b4712a549d4959693cd71
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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