Water → HCID 89814045, compound

HRID 522731Notes

Reaction equation

HRID 522731 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=O.[CH3:16]N1C=CN=C1.O>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13](=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 13901-MethylimidazoleHCID 68986110HCID 68986110, compound

Product 1

HCID 89814045HCID 89814045, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Treat a solution of 2-(2-bromo-4-fluoro-5-nitrophenyl)acetic acid (30.0 g, 0.11 mol) in acetic anhydride (30 mL) with 1-methylimidazole (4.5 g, 55 mmol), stir at RT for 2 h, treat with water, stir for 5 min, and extract with EtOAc. Wash the combined organics with water, saturated. Na2CO3, then brine, dry over Na2SO4, concentrate and purify via silica gel chromatography (EtOAc/petroleum ether) to afford the title compound (12 g, 40% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.19 (d, J=8.0 Hz, 1H), 8.02 (d, J=10.8 Hz, 1H), 4.09 (s, 2H), 2.23 (s, 3H).

Workup

  1. stirringstir for 5 min
  2. extractionextract with EtOAc
  3. washWash the combined organics with water
  4. dry with materialNa2CO3, then brine, dry over Na2SO4
  5. concentrationconcentrate
  6. custompurify via silica gel chromatography (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-67d8a3699d3d4d8cbbbac467e3b7bc40
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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