Ethyl Bromide → HCID 23130247, compound

HRID 1874091Notes

Reaction equation

HRID 1874091 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:2]([O:1][CH2:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 6332Ethyl Bromide2×HCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 23130247HCID 23130247, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of methyl 3-hydroxyl-4-nitrobenzoate (25.1 g, 125 mmol) and bromoethane (20 mL, 263 mmol) in 200 mL ACN is cooled to 15° C. Potassium carbonate (54.4 g, 390 mmol) is added and the reaction mixture is stirred overnight at 60° C. Additional bromoethane (10 mL, 131 mmol) is added and the reaction mixture is stirred overnight at 95° C. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is triturated with ACN and dried in vacuo. Yield: 26.5 g.

Workup

  1. stirringthe reaction mixture is stirred overnight at 95° C
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is triturated with ACN
  5. customdried in vacuo

Sources & evidence

ORD record
ord-900ae1ae8ffa485ca22d632905153453
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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