Benzoyl chloride → HCID 67235106, compound

HRID 1851723Notes

Reaction equation

HRID 1851723 reaction equation
[CH2:1]([CH:3]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:2].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH2:1]([CH:3]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][N:5]1[C:6]2[CH:7]=[CH:8][C:9]([C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:29])=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 162178689-(2-Ethylhexyl)-9H-carbazole

Product 1

HCID 67235106HCID 67235106, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-(2-ethyl-hexyl)-9H-carbazole (7.0 g, 0.025 mol) in dichloromethane (30 ml), benzoyl chloride (4.5 g, 0.0525 mol) was added and stirred for 15 minutes at room temperature. Aluminium chloride (7.3 g, 0.055 mol) was added in portions while the temperature was maintained below 30° C. The reaction mixture was allowed to stir at room temperature for 15 hours. The reaction mixture was poured into ice (150 g) and distilled water (100 ml) and diluted with dichloromethane (200 ml). The organic layer was separated and washed with a saturated solution of sodium bicarbonate (250 ml) and a saturated solution of sodium chloride (250 ml). The organic layer was dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residual solid was purified on a Prochrom LC80 Column using ethyl acetate/n-hexane (20/80) as eluent. TLC shows a yellow fluorescent product with Rf-value of 0.48 in dichloromethane as eluent. Evaporation of the pooled fractions yielded 1.5 g of [9-(2-ethyl-hexyl)-9H-carbazol-3-yl]-phenyl-methanone.

Workup

  1. temperaturewas maintained below 30° C
  2. stirringto stir at room temperature for 15 hours
  3. distillationdistilled water (100 ml)
  4. additiondiluted with dichloromethane (200 ml)
  5. customThe organic layer was separated
  6. washwashed with a saturated solution of sodium bicarbonate (250 ml)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe residual solid was purified on a Prochrom LC80 Column
  11. customEvaporation of the pooled fractions

Sources & evidence

ORD record
ord-f4609a1c88ea4f3d8781b449d0c223a0
Source dataset
uspto-grants-2015_02
Patent number
US08957224B2

Reaction notes

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