2,4-Difluoronitrobenzene → HCID 58707323, compound

HRID 2426011Notes

Reaction equation

HRID 2426011 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].C(N(CC)C(C)C)(C)C>C(#N)C>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH:17][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 457587Benzenemethanamine, 3-bromo-

Product 1

HCID 58707323HCID 58707323, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Difluoronitrobenzene (2.9 g, 18.1 mmol), 3-Bromobenzylamine (2.6 g, 18.1 mmol) and N,N-diisopropylethylamine (2.4 g, 18.1 mmol) were stirred in acetonitrile (25 mL) at room temperature for 2 hours. The solvent was evaporated and the crude mixture was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated in vacuo to collect the title compound (4.8 g, 95% yield). 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 8.25 (dd, 1H), 7.32-7.21 (m, 4H), 6.41 (m, 2H), 4.50 (d, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated in vacuo

Sources & evidence

ORD record
ord-1d47815786dd4ac7b4bc8a03611de7db
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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