2-Fluorobenzoyl chloride → HCID 86690528, compound

HRID 2172362Notes

Reaction equation

HRID 2172362 reaction equation
[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][N:5]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14]([CH:22]=[O:23])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][N:5]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14]([CH:22]=[O:23])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:35](=[O:36])[C:34]1[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=1[F:32])[CH:10]=2)[CH3:2]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86690529HCID 86690529, compound

Product 1

HCID 86690528HCID 86690528, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole-5-carbaldehyde (1.40 g, 3.91 mmol) in CH2Cl2 (20 ml) are added AlCl3 (1.21 g, 9.07 mmol) and 2-fluorobenzoyl chloride (0.70 g, 4.41 mmol) at 0° C. After stirring at room temperature for 17 hours, the reaction mixture is poured into ice-water. The crude product is extracted with CH2Cl2 and washed with water and brine. After drying over MgSO4 and concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain an off-white solid (1.76 g, 93%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82-0.91 (m), 1.17-1.43 (m), 2.24 (m), 4.69 (m), 7.25 (t), 7.33 (t), 7.57-7.77 (m), 8.12 (d), 8.57 (d), 8.60 (s), 8.64 (s), 9.63 (d), 10.38 (s); 19F-NMR spectrum (CDCl3). δ [ppm]−111.97.

Workup

  1. extractionThe crude product is extracted with CH2Cl2
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4 and concentration
  4. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-09cfd47a60e54943acf31a2236a94405
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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