Water → Ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoate

HRID 1183583Notes

Reaction equation

HRID 1183583 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].C([O-])([O-])=O.[Cs+].[Cs+].[CH:28]1([CH2:31]Br)[CH2:30][CH2:29]1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[O:8][CH2:31][CH:28]1[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 57995502Ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate

Product 1

HCID 57995564Ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoateYield 64.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate (4.1 g, 11.26 mmol) was taken in 50 ml of DMSO and to it added Cs2CO3 (3.02 g, 12.39 mmol). The reaction mixture was stirred at room temperature for 15 minutes and then added cyclopropylmethyl bromide (1.67 g, 12.39 mmol) dropwise. After completion of addition, the reaction mixture was stirred at 70° C. for 4 h. After completion of the reaction, it was poured into water (200 ml) and extracted with ethyl acetate (100 ml×3). The ethyl acetate layer was washed with 1N HCl, water and finally brine solution. The organic layer was then distilled off and the crude residue was purified by column chromatography using Ethyl acetate:hexane (1:3) as eluent provided 3 g of ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-nitrophenyl)-4-methylpentanoate. 1H NMR (CDCl3): δ 8.20 (s 1H), 7.20 (s, 1H), 4.15 (q, 2H), 3.60 (t, 1H), 3.45 (d, 2H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.20 (t, 3H), 1.00 (m, 6H), 0.35-0.25 (m, 5H). Mass: (414, M+1,100%).

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at 70° C. for 4 h
  3. customAfter completion of the reaction, it
  4. extractionextracted with ethyl acetate (100 ml×3)
  5. washThe ethyl acetate layer was washed with 1N HCl, water and finally brine solution
  6. distillationThe organic layer was then distilled off
  7. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-26a9e20519f24b4eb4381f712c110e65
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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