1-Bromo-2-Chloroethane → 5-(2-chloroethylsulfanyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 400098Notes

Reaction equation

HRID 400098 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([SH:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].[Na].Br[CH2:23][CH2:24][Cl:25]>C(O)C.C1(C)C=CC=CC=1>[Cl:25][CH2:24][CH2:23][S:16][CH:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

7

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 1894394510,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-thiol

Product 1

HCID 189439415-(2-chloroethylsulfanyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of the above crude thiol (4.53 g, 0.020 mol) in absolute ethanol (7 ml) was added dropwise to a stirred solution of sodium ethoxide, freshly prepared from absolute ethanol (25 ml) and sodium (0.46 g, 0.020 mol). Stirring was continued for 0.5 h at ambient temperature. 1-Bromo-2-chloroethane (8.60 g, 0.060 mol) was added dropwise and the reaction mixture was stirred at ambient temperature for 16 h. The mixture was diluted with toluene (20 ml) and filtered. The filtrate was evaporated in vacuo and stripped with toluene, affording 5.72 g (99%) of crude 5-(2-chloroethylsulfanyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as an oil.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 16 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7b13d285506846408eebb3b50660a713
Source dataset
uspto-grants-1998_10
Patent number
US05827856

Reaction notes

Loading…