4-Methylbenzenethiol → HCID 11218777, compound

HRID 440752Notes

Reaction equation

HRID 440752 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1>CS(C)=O.[Cu]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 114644-Bromobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 11218777HCID 11218777, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 6.0 g of 4-mercapto-toluene and 9.2 g of potassium t-butoxide is stirred at room temperature under a nitrogen atmosphere in 50 ml of dimethylsulfoxide for 10 minutes followed by the addition of 11.5 g of 4-bromobenzoic acid and 0.2 g of copper metal. The reaction mixture is stirred at 210° C. for 16 hours. The reaction mixture is poured over crushed ice and filtered through diatomaceous earth. The filtrate is acidified with HCl until pH 2. The resulting solid is collected, washed with water and 60 ml of petroleum ether to give 8.5 g of the desired product, m.p. 105°-107° C., M+H=245.

Workup

  1. additionThe reaction mixture is poured
  2. customover crushed ice
  3. filtrationfiltered through diatomaceous earth
  4. customThe resulting solid is collected
  5. washwashed with water and 60 ml of petroleum ether

Sources & evidence

ORD record
ord-8c29534e845143df9d1acac3f38416a1
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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