Methyl iodide → HCID 70980247, compound

HRID 1475459Notes

Reaction equation

HRID 1475459 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21])([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:25]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7559Methyl phenylacetateHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 70980247HCID 70980247, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of phenyl-acetic acid methyl ester (4 g, 27.3 mmol) and 4-bromo-1-fluoro-2-nitro-benzene (5 g, 22.7 mmol) in DMF (30 mL) was slowly added to a suspension of NaH (60% in mineral oil, 3 g, 77.1 mmol) in DMF (80 mL) at 0° C. under N2. The reaction was then stirred for 3 h at room temperature. MeI (5.6 mL, 91 mmol) was then added and the reaction was stirred overnight at the same temperature. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. Chromatography (10% EtOAc in 40-60 petroleum ether) gave the title compound (2.6 g) as an orange semi-solid. 1H NMR (DMSO-d6): 8.21-8.14 (1H, m), 7.86-7.77 (1H, m), 7.44-7.36 (5H, m), 6.84 (1H, d), 3.53 (3H, s), 2.06 (3H, s).

Workup

  1. stirringthe reaction was stirred overnight at the same temperature
  2. customThe reaction was quenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a15dcb503abf42c7a053b9c9d6069aef
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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