1-Fluoro-2-nitrobenzene → 3,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indole

HRID 12388Notes

Reaction equation

HRID 12388 reaction equation
[CH3:1][C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>C(Cl)Cl>[CH3:1][C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 118049123,3-Dimethylindoline

Product 1

HCID 593377113,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
175 °C

Procedure

To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175° C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 10% EtOAc in hexane over 30 min as eluting solvent to afford 2d (360 mg, 95%) as an oil. MS (ES) m/z 269 [M+H]+.

Workup

  1. washwashed with 1N HCl
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated under reduced pressure
  4. custompurified by column chromatography
  5. customover 30 min
  6. washas eluting solvent

Sources & evidence

ORD record
ord-c8b49cfec5fa471483c52646642798ca
Source dataset
uspto-grants-2010_06
Patent number
US07728008B2

Reaction notes

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