Potassium Carbonate → 1239278-72-8

HRID 2172582Notes

Reaction equation

HRID 2172582 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:21]1([CH2:24]Br)[CH2:23][CH2:22]1>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH2:24][CH:21]2[CH2:23][CH2:22]2)[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 594437631239278-72-8

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-Hydroxy-4-nitro-benzoic acid methyl ester (10.5 g) was dissolved in dry DMF (150 ml) under N2 atmosphere. K2CO3 (24.3 g), KI (2.6 g) and cyclopropylmethylbromide (10.3 ml) were added and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was diluted with water (300 ml) and extracted with Et2O (2×200 ml); the combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation to yield 12.7 g of the desired intermediate.

Workup

  1. extractionextracted with Et2O (2×200 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-16eced57828b4f898202ede9b354dd35
Source dataset
uspto-grants-2015_06
Patent number
US09056176B2

Reaction notes

Loading…