4-Chloro-3-[(carboxymethyl)sulfonyl]benzoic acid methyl ester → Methyl 4-chloro-3-(methylsulfonyl)benzoate

HRID 1532284Notes

Reaction equation

HRID 1532284 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([S:11]([CH2:14]C(O)=O)(=[O:13])=[O:12])[CH:5]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=1

Participants

3

Reactant 1

HCID 540904054-Chloro-3-[(carboxymethyl)sulfonyl]benzoic acid methyl ester

Product 1

HCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chloro-3-[(carboxymethyl)sulfonyl]benzoic acid methyl ester (5.6 g) was mixed with pyridine (10 mL) and the mixture was refluxed for 30 min and then cooled to room temperature. The product was precipitated by adding water (30 mL). The precipitate was filtered, washed with water and dried (yield 2.5 g). 1H-NMR (400 MHz, DMSO-d6) d=3.43 (s, 3H), 3.92 (s, 3H), 7.92 (d, J=8.2 Hz, 1H), 8.24 (dd, J=8.2 Hz, 2.2 Hz, 1H), 8.53 (d, J=2.2 Hz, 1H).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. customThe product was precipitated
  3. additionby adding water (30 mL)
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried (yield 2.5 g)

Sources & evidence

ORD record
ord-2620efac3d594871b2efc815fec98769
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

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