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

HRID 1930421Notes

Reaction equation

HRID 1930421 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH2:15][C:16]([OH:18])=[O:17].[CH3:19][CH2:20]O>>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 8271282-(2-Chloro-5-nitrophenyl)acetic acid

Product 1

HCID 22970611Ethyl 2-(2-chloro-5-nitrophenyl)acetateYield 99%

Procedure

Thionyl chloride (16.7 g, 0.14 mol) was added dropwise to a 0° C. solution of (2-chloro-5-nitro-phenyl)acetic acid (15 g, 0.07 mol) in EtOH (300 mL) and the resultant mixture was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure and the residue was poured into ice water, and extracted with EtOAc (2×300 mL). The combined organics were washed with brine and saturated NaHCO3 solution, were dried over Na2SO4, and were concentrated in vacuo to give ethyl 2-(2-chloro-5-nitrophenyl)acetate (17 g, 99% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.35 (d, J= 2.8 Hz, 1 H), 8.12 (dd, J=8.4, 2.8 Hz, 1 H), 7.72 (d, J=8.4 Hz, 1 H), 4.10 (q, J=7.2 Hz, 2 H), 3.96 (s, 2 H), 1.15 (t, J=7.2 Hz, 3 H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured into ice water
  4. extractionextracted with EtOAc (2×300 mL)
  5. washThe combined organics were washed with brine and saturated NaHCO3 solution
  6. dry with materialwere dried over Na2SO4
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-3574ae1c32c343519e66ee7978f87fd1
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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