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

HRID 1257191Notes

Reaction equation

HRID 1257191 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 drop-wise 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, the residue poured into ice water, and extracted with EtOAc (2×). The combined organics were washed with brine, then satd. NaHCO3, dried over Na2SO4 and 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, 1H), 8.12 (dd, J=8.4, 2.8 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 4.10 (q, J=7.2 Hz, 2H), 3.96 (s, 2H), 1.15 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue poured into ice water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialNaHCO3, dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edf26bb38b12406d8cf9e69775898f49
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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