Ethanol → Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate

HRID 1430467Notes

Reaction equation

HRID 1430467 reaction equation
[Cl: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:14].S(Cl)(Cl)(=O)=O.[CH3:21][CH2:22]O>>[Cl: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][CH2:21][CH3:22])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 24648Sulfuryl chlorideHCID 689833332-(2-Chloro-4-fluoro-5-nitrophenyl)acetic acid

Product 1

HCID 68984950Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetateYield 98%

Procedure

A 0° C. solution of 2-(2-chloro-4-fluoro-5-nitrophenyl)acetic acid (20.5 g, 88 mmol) in EtOH (150 mL) was treated with sulfuryl dichloride (21 g, 0.17 mol), then heated to reflux for 1 h. The reaction mixture was concentrated under reduced pressure and treated with satd. Na2CO3 to pH 7-8. The resultant mixture was extracted with EtOAc (3×) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated to give ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate (22.5 g, 98% yield). 1H NMR (400 Hz, DMSO-d6): δ 8.32 (d, J=8.0 Hz, 1H), 7.91 (d, J=11.2 Hz, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.92 (s, 2H), 1.17 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiontreated with satd
  5. extractionThe resultant mixture was extracted with EtOAc (3×)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-455861b73e244fe9b0621bece7ae58e7
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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