Water → 5-Chloro-2-methoxybenzene-1-thiol

HRID 1616943Notes

Reaction equation

HRID 1616943 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([S:8](Cl)(=O)=O)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([SH:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 127727855-Chloro-2-methoxybenzene-1-thiolYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-2-methoxy-benzenesulfonyl chloride (1.0 g, 4.1 mmol) and triphenylphosphine (3.81 g, 14.5 mmol) were dissolved in THF (10 ml). Water (1.3 ml) was added and the mixture was stirred for 2 h at room temperature. The mixture was partitioned between 2N aqueous NaOH and diethylether. The aqueous phase was acidified to pH 1 with concentrated HCl and then extracted twice with methylene chloride. The combined organic layers were dried over MgSO4 and the solvent was evaporated to afford the desired product (690 mg), which was used in the next reaction step without further purification. MS m/z: 175 [M+H]+

Workup

  1. customThe mixture was partitioned between 2N aqueous NaOH and diethylether
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fcabea78eea64ed6a948b260b4530ca7
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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