Nitromethane → 2-Bromo-1-cyclopropylmethoxy-3-(2-nitro-vinyl)-benzene

HRID 523996Notes

Reaction equation

HRID 523996 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:9]=1[O:10][CH2:11][CH:12]1[CH2:14][CH2:13]1)C=O.[N+:15]([CH3:18])([O-:17])=[O:16].[C:19]([O-])(=O)C.[NH4+]>CC(O)=O>[Br:1][C:2]1[C:3]([CH:19]=[CH:18][N+:15]([O-:17])=[O:16])=[CH:4][CH:5]=[CH:6][C:9]=1[O:10][CH2:11][CH:12]1[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 597250443-Bromo-2-(cyclopropylmethoxy)benzaldehyde

Product 1

HCID 1317355752-Bromo-1-cyclopropylmethoxy-3-(2-nitro-vinyl)-benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

380 mg (1.49 mmol) 5-Bromo-6-cyclopropylmethoxy-benzaldehyde (example XIX), 239 μL (4.47 mmol) nitromethane and 115 mg (1.49 mmol) ammonium acetate in 1.2 mL AcOH are stirred at 100° C. for 2 h. The reaction mixture is cooled to r.t. and quenched by the addition of 4 mL MeOH and 0.9 mL water. After stirring at r.t. for 1 h the precipitate is filtered off and dried at 40° C.

Workup

  1. customquenched by the addition of 4 mL MeOH and 0.9 mL water
  2. filtrationis filtered off
  3. customdried at 40° C.

Sources & evidence

ORD record
ord-b11a8b9952fd47b09167a0a3d0bede74
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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