4-Phenylbenzyl chloride → HCID 18799543, compound

HRID 1637651Notes

Reaction equation

HRID 1637651 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[H-].[Na+].[C:17]1([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[C:23]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:24]=[CH:25][C:26]([CH2:27][N:6]2[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 2524463-Bromocarbazole

Product 1

HCID 18799543HCID 18799543, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-9H-carbazole (7.38 g, 30 mmol, prepared as described in Tetrahedron (1992), 48, 4779) in N,N-dimethylformamide (200 ml) was added portion wise sodium hydride (1.6 g, 39 mmol, 60% in mineral oil) during 15 min. After stirring at room temperature for 1 h, 4-phenyl-benzylchloride (6.21 g, 30 mmol) was added portion wise during 10 min. The resulting reaction mixture was stirred at room temperature for 20 h poured onto water (300 ml) and stirred for 4 h. The precipitate was filtered off, washed with water (3×150 ml) and dried in vacuo at 50° C. for 18 h. The crude product was washed with heptane, filtered off and dried in vacuo at 50° C. affording 12 g (100%) of 9-(biphenyl-4-ylmethyl)-3-bromo-9H-carbazole as a solid.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 20 h
  3. additionpoured onto water (300 ml)
  4. stirringstirred for 4 h
  5. filtrationThe precipitate was filtered off
  6. washwashed with water (3×150 ml)
  7. customdried in vacuo at 50° C. for 18 h
  8. washThe crude product was washed with heptane
  9. filtrationfiltered off
  10. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-1f75e2f48751436284b7725695086c52
Source dataset
uspto-grants-2000_03
Patent number
US06043247

Reaction notes

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