1-Bromo-2-methylpropane → HCID 23023853, compound

HRID 851858Notes

Reaction equation

HRID 851858 reaction equation
[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].[OH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 23023853HCID 23023853, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Isobutyl bromide (10.5 mL, 95.8 mmol) was added to a suspension of methyl 4-hydroxy-3-nitrobenzoate (6.26 g, 31.8 mmol) and potassium carbonate (13.2 g, 95.5 mmol) in dry DMF (40 mL). The resulting mixture was stirred at 90° C. for 44 hours and then cooled to room temperature. Subsequently, ice-water (80 mL) was added to the cooled mixture. The precipitated crystalline product was collected by filtration, washed with water (50 mL), and dried for 30 min in air. The dried crystalline product was then washed with hexane (40 mL), and dried in air to give 7.03 g (yield 87%) of the desired compound in the form of a pale orange crystalline product.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitated crystalline product was collected by filtration
  3. washwashed with water (50 mL)
  4. customdried for 30 min in air
  5. washThe dried crystalline product was then washed with hexane (40 mL)
  6. customdried in air

Sources & evidence

ORD record
ord-3fcf96dfff4447e282df2f0c1bd68b9d
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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