Methyl phenylacetate → HCID 117599770, compound

HRID 513241Notes

Reaction equation

HRID 513241 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17](F)[CH:16]=1>CN(C=O)C.[NH4+].[Cl-]>[CH3:3][O:4][C:5](=[O:13])[CH:6]([C:19]1[CH:20]=[C:15]([Br:14])[CH:16]=[CH:17][C:18]=1[N+:21]([O-:23])=[O:22])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 7559Methyl phenylacetateHCID 24758Sodium hydrideHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 117599770HCID 117599770, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

NaH (1.6 g, 63 mmol) is added portion wise to a solution of phenyl-acetic acid methyl ester (9.0 g, 60 mmol) in DMF (150 mL) at −15° C. and stirred at this temperature for 3 hours. 4-Bromo-2-fluoro-1-nitro-benzene (6.57 g, 30.0 mmol) is added to the above mixture at −15° C. The mixture is warmed to room temperature slowly and stirred for 24 hours. The mixture is diluted with saturated aqueous NH4Cl solution and extracted with ethyl acetate (3×100 mL). The combined organic phase is washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue is purified by chromatography (ethyl acetate:petroleum ether=1:20) to give the desired product.

Workup

  1. stirringstirred for 24 hours
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic phase is washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography (ethyl acetate:petroleum ether=1:20)

Sources & evidence

ORD record
ord-cbe811e690c04da3b7c6009eec5d0d11
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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