Sodium Carbonate → N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17275

Reaction equation

HRID 17275 reaction equation
[Br:1][C:2]1[C:7]([O:8]C)=[C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([C:17]#[N:18])=[C:4]([CH3:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.BrB(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:13])[CH3:14])[C:5]([C:17]#[N:18])=[C:4]([CH3:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 86630799N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

Product 1

HCID 86630803N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamideYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide (I-12) (630 mg, 1.41 mmol) was dissolved in dichloromethane (dewatered, 20 ml) under nitrogen atmosphere, cooled at −70° C. in a dry ice-methanol bath. 1 M tribromoborane (dichloromethane solution) (4.23 ml) was dropwise added to it at −70° C. to −68° C., followed by stirring for 2 hours with heating up to 0° C. The reaction liquid was diluted with cold water, followed by pH control at 6 to 7 by addition of aqueous 10% sodium carbonate solution. The organic matter was extracted with ethyl acetate, washed with saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2) to obtain the entitled compound (503 mg, 82%) as a pale yellow solid.

Workup

  1. temperaturewith heating up to 0° C
  2. customThe reaction liquid
  3. extractionThe organic matter was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

Sources & evidence

ORD record
ord-b841381e700d49a1be971cf84131fb70
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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