2-Fluoroaniline → HCID 28581760, compound

HRID 2237511Notes

Reaction equation

HRID 2237511 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C([Li])CCC.[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br)([O-:16])=[O:15]>O1CCCC1.C(OCC)C>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 95842-FluoroanilineHCID 77569alpha-Bromo-2-nitrotolueneHCID 178418339Butyllithium

Product 1

HCID 28581760HCID 28581760, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-fluoroaniline (6.8 mL, 70 mmol) in tetrahydrofuran (200 mL) was cooled to −78° C. and treated with n-butyllithium (31 mL of a 2.5 M solution in hexanes, 77 mmol). After 1 h, the reaction mixture was treated with a solution of 2-nitrobenzylbromide (15.1 g, 70 mL) in tetrahydrofuran (50 mL), and warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with ethyl ether (500 mL), and washed with H2O (500 mL), and evaporated. Flash chromatography (SiO2, 5-20% ethyl acetate/hexanes) provided 2-fluoro-N-(2-nitrobenzyl)aniline (13.4 g) as a yellow solid:

Workup

  1. washwashed with H2O (500 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-05ad863abe0c465f9d03f58ba7e09b6f
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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