4-Fluorobenzyl chloride → HCID 19384468, compound

HRID 2399798Notes

Reaction equation

HRID 2399798 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH2:12][C:13]3[C:17]=2[N:16]=[C:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:14]=32)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH:12]([CH2:29][C:28]3[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=3)[C:13]3[C:17]=2[N:16]=[C:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:14]=32)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 19384476HCID 19384476, compound

Product 1

HCID 19384468HCID 19384468, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,2,3,4-tetrahydro-6-(phenylmethoxy)-9H-dibenzo[b,d]pyrrole (2.77 g) in dimethylformamide (20 mL) was stirred under argon at room temperature and treated with a 55% oil dispersion of sodium hydride in mineral oil (0.48 g). After stirring for ten minutes, a solution of 4-fluorobenzyl chloride (1.73 g) in dimethylformamide (5 mL) was added and the mixture was stirred for an additional 30 minutes. The solvent was removed by evaporation and the residue was mixed with water and extracted with dichloromethane. The organic phase was dried over sodium sulfate, concentrated and the residue was purified by HPLC chromatography (eluting system: dichloromethane-hexane 1:2) and crystallization from ether-hexane to produce 2.9 g (75%) of 1,2,3,4-tetrahydro-6-(phenylmethoxy)-9-[(4-fluorophenyl)methyl]-9H-dibenzo[b,d]pyrrole, mp 134°-135° C.

Workup

  1. stirringthe mixture was stirred for an additional 30 minutes
  2. customThe solvent was removed by evaporation
  3. additionthe residue was mixed with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by HPLC chromatography (eluting system: dichloromethane-hexane 1:2) and crystallization from ether-hexane

Sources & evidence

ORD record
ord-3d4d6b0a9f334ee6b3e9046e3fb8e3dd
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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