Butyl bromide → HCID 67154048, compound

HRID 1400153Notes

Reaction equation

HRID 1400153 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH3:22].[Cl-].[NH4+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:19][CH2:20][CH2:21][CH3:22])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 67154048HCID 67154048, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

10.46 g of ethyl 4-nitrophenylacetate are dissolved in 30 ml of DMF, added dropwise to a suspension of 2.0 g of sodium hydride in 20 ml of DMF with ice-cooling and stirred for 30 min. 5.394 ml of 1-bromobutane in 20 ml of DMF are subsequently added, and the mixture is stirred at 23° C. for 12 h. The reaction mixture is subsequently stirred into 100 ml of saturated ammonium chloride solution. The mixture is washed 4 times with 100 ml of ethyl acetate each time, the combined organic phases with 100 ml of sodium chloride solution, dried over sodium sulfate and, after filtration, evaporated to dryness in vacuo. The residue is purified by column chromatography (reversed phase). Yield: 11 g (83%) of ethyl 2-(4-nitrophenyl)hexanoate; LC-MS retention time: 2.44 min (“nonpolar” gradient).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at 23° C. for 12 h
  3. washThe mixture is washed 4 times with 100 ml of ethyl acetate each time
  4. dry with materialthe combined organic phases with 100 ml of sodium chloride solution, dried over sodium sulfate
  5. filtrationafter filtration
  6. customevaporated to dryness in vacuo
  7. customThe residue is purified by column chromatography (reversed phase)

Sources & evidence

ORD record
ord-77dc743c028a40e3b84a7afe4dbdb1b0
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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