Water → 2-Chloro-4-fluorobenzenesulfonic acid, 3-[2-(4-cyanophenyl)ethoxy]-5-chlorophenyl ester

HRID 325052Notes

Reaction equation

HRID 325052 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[CH:15]=[C:16]([OH:31])[CH:17]=[C:18]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:19]=1.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([O:31][C:16]1[CH:15]=[C:14]([Cl:13])[CH:19]=[C:18]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:17]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 5228462-Chloro-4-fluorobenzene-1-sulfonyl chlorideHCID 220335343-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol

Product 1

HCID 572825492-Chloro-4-fluorobenzenesulfonic acid, 3-[2-(4-cyanophenyl)ethoxy]-5-chlorophenyl esterYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloro-4-fluorobenzenesulfonyl chloride (1.16 g; 5.0 mmol) was added to a cold solution (ice:water temperature) of 3-chloro-5-[2-(4-cyanophenyl)-ethoxy]phenol (0.689 g; 2.5 mmol; from step (ii) above) in pyridine (8 mL). The temperature was allowed to rise (slowly) to ambient overnight. The mixture was re-cooled (ice:water temperature) and ice was added to the reaction flask. After stirring for 4 hours, the pyridine was removed in vacuo. CH2Cl2 was then added and the organic layer was washed with aqueous KHSO4 and water. Drying (MgSO4), evaporation of the solvent and purification by flash chromatography (SiO2; CH2Cl2) afforded 0.84 g (72%) of the sub-title compound.

Workup

  1. customto ambient overnight
  2. additionwas added to the reaction flask
  3. customthe pyridine was removed in vacuo
  4. additionCH2Cl2 was then added
  5. washthe organic layer was washed with aqueous KHSO4 and water
  6. customDrying
  7. custom(MgSO4), evaporation of the solvent and purification by flash chromatography (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-c1f1c3cb484f4767b80e35c1d18b489a
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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