Ethyl bromoacetate → HCID 69549673, compound

HRID 1743856Notes

Reaction equation

HRID 1743856 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:11])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22236595HCID 22236595, compound

Product 1

HCID 69549673HCID 69549673, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of [2-(4-fluoro-2-nitro-phenyl)-ethyl]-methyl-amine (10.4 g, 0.053 mole) and ethyl bromoacetate (8.8 g, 0.053 mole) in acetonitrile (200 mL) containing potassium carbonate (3.64 g, 0.026 mole) was stirred at room temperature overnight. The mixture was evaporated in vacuo, water was added to the residue and then extracted with dichloromethane (2×200 mL). The combined organic layers were washed with saturated sodium chloride (300 mL), dried and concentrated. Purification by flash column chromatography (silica gel, methylene chloride:hexanes 1:1 to methylene chloride) provided 10.0 g of the title compound as a light brown oil. 1H NMR (CDCl3): 7.65 δ (dd, 1H); 7.40 δ (dd, 1H); 7.25 δ (dd, 1H); 4.20 δ (m, 2H); 3.30 δ (s, 2H); 3.05 δ (t, 2H); 2.80 δ (t, 2H); 2.45 δ (s, 3H); 1.25 δ (t, 3H).

Workup

  1. customThe mixture was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with dichloromethane (2×200 mL)
  4. washThe combined organic layers were washed with saturated sodium chloride (300 mL)
  5. customdried
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, methylene chloride:hexanes 1:1 to methylene chloride)

Sources & evidence

ORD record
ord-c151f53dad344ad68ef1156f7a22202a
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

Loading…