Methanethiol → HCID 21320299, compound

HRID 262227Notes

Reaction equation

HRID 262227 reaction equation
[Br:1][C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH3:19])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.BrC1[O:22]C2C=CC(CBr)=CC=2C=1C1C=CC=CC=1.CS.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][S:18]([CH3:19])=[O:22])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 70297m-Chloroperbenzoic acidHCID 20333828HCID 20333828, compoundHCID 21320278HCID 21320278, compound

Product 1

HCID 21320299HCID 21320299, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred, cold solution of 7.8 g. of 2-bromo-5-methylthiomethyl-3-phenylbenzofuran (prepared by reacting 2-bromo-5-bromomethyl-3-phenylbenzofuran with methyl mercaptan according to the procedure of Example 18 hereof) in 100 ml. of chloroform is added dropwise 4.73 g. of 3-chloroperbenzoic acid in chloroform at 0° C. After three hours an addition 0.3 g. of the peracid is added and 30 minutes later the solution is washed with cold 5 percent sodium hydroxide solution, then with saturated sodium chloride solution and dried. Evaporation provides a residue which is recrystallized from a chloroform-hexane mixture to provide 2-bromo-5-methylsulfinylmethyl-3-phenylbenzofuran. The structural assignment is confirmed by infrared and nuclear magnetic resonance spectral analysis.

Workup

  1. customat 0° C
  2. additionAfter three hours an addition 0.3 g
  3. washis washed with cold 5 percent sodium hydroxide solution
  4. dry with materialwith saturated sodium chloride solution and dried
  5. customEvaporation
  6. customprovides a residue which
  7. customis recrystallized from a chloroform-hexane mixture

Sources & evidence

ORD record
ord-7fddbe14c64848fca286907601e41992
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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