Acetyl chloride → HCID 68452867, compound

HRID 2356183Notes

Reaction equation

HRID 2356183 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:30](=[O:32])[CH3:31])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([F:16])=[CH:18][CH:19]=1)[CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 6836N-ethyl carbazoleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 68452867HCID 68452867, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-ethylcarbazole (5.00 g; 25.60 mmol) in CH2Cl2 (40 ml) is added 4-fluorobenzoyl chloride (4.06 g; 25.60 mmol) and AlCl3 (3.41 g; 25.6 mmol) at 0° C. After stirring for 4 h at room temperature, acetyl chloride (2.01 g; 25.60 mmol) and AlCl3 (3.41 g; 25.6 mmol) are added at 0° C. This reaction mixture is stirred at room temperature for overnight. After the reaction is completed, the reaction mixture is poured into ice-water. Then, the product is extracted with CH2Cl2. The organic layer is washed with H2O, saturated NaHCO3 aq. solution and brine, followed by drying over anhydrous MgSO4. Condensation under reduced pressure and washing with tert-Butyl methyl ether (TBME) affords a gray solid as crude product (7.20 g). The compound is used for the next reaction without further purification. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.50 (t, 3H), 2.73 (s, 3H), 4.45 (q, 2H), 7.21 (d, 2H), 7.49 (dd, 2H), 7.89 (dd, 2H), 8.05 (dd, 1H), 8.19 (dd, 1H), 8.59 (d, 1H), 8.78 (d, 1H).

Workup

  1. stirringThis reaction mixture is stirred at room temperature for overnight
  2. extractionThen, the product is extracted with CH2Cl2
  3. washThe organic layer is washed with H2O, saturated NaHCO3 aq. solution and brine
  4. dry with materialby drying over anhydrous MgSO4
  5. customCondensation under reduced pressure
  6. washwashing with tert-Butyl methyl ether (TBME)

Sources & evidence

ORD record
ord-9666186c900e40e2b6345147f89053cf
Source dataset
uspto-grants-2010_07
Patent number
US07759043B2

Reaction notes

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