Sodium Sulfide → Benzo(c)thiophene, 1,3-dihydro-

HRID 1856485Notes

Reaction equation

HRID 1856485 reaction equation
Br[CH:2](Br)[C:3]1[C:4]([CH3:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[S-2:11].[Na+].[Na+]>C(O)C>[CH2:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][S:11]1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 6390401-(Dibromomethyl)-2-methylbenzene

Product 1

HCID 137608Benzo(c)thiophene, 1,3-dihydro-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compounds of formula 4 where n is 0, 1 or 2 are prepared by a modification of the procedure of ##STR13## Oliver, et al., in Chem. and Ind., 1024 (1965). α,α-Dibromo-o-xylene is reacted with sodium sulfide in ethanol to form 1,3-dihydrobenzo[c]thiophene. The thiophene compound is oxidized to the corresponding dioxide by means of hydrogen peroxide, m-chloroperzenxoic acid or other suitable oxidants or to the monoxide (Can. J. Chem., 51, 4082 (1973) using sodium metaperoidate.

Workup

  1. customare prepared by a modification of the procedure of ##STR13## Oliver, et al., in Chem

Sources & evidence

ORD record
ord-6c9b7de8507a44769bea48a9d8192380
Source dataset
uspto-grants-1980_08
Patent number
US04219648

Reaction notes

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