Dimethylformamide → HCID 59820827, compound

HRID 1363659Notes

Reaction equation

HRID 1363659 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenolHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 59820827HCID 59820827, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(tert-butyl)benzyl bromide (6.252 g, 27.522 mmol), 4-bromo-2-nitrophenol (5.0 g, 22.934 mmol), potassium carbonate (12.679 g, 91.736 mmol) and dimethylformamide (40 ml) was stirred at 50° for 3 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane to give the title compound (8.1 g, 97.0%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. washwas washed with n-hexane

Sources & evidence

ORD record
ord-79ac7e9e618140c79b9f60ff2b1311b3
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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