Dichloromethane → 2-(1-Phenyl-cyclohexyl)-thiophene

HRID 1170562Notes

Reaction equation

HRID 1170562 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.ClCCl>Br.C(O)(=O)C>[C:1]1([C:7]2([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8030ThiopheneHCID 130431-Phenylcyclohexene

Product 1

HCID 669681192-(1-Phenyl-cyclohexyl)-thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Phenyl cyclohexene (50 mg) and thiophene (100 mg) were dissolved in 33% HBr in acetic acid (0.5 mL). The mixture was stirred at room temperature over night. Tlc indicated full conversion of the starting material. Dichloromethane (10 mL) was added. The organic phase was washed with saturated NaHCO3 (3×10 mL), dried Na2SO4 and concentrated in vacuo. The desired product was afforded after flash chromatography (eluent: dichloromethane). Yield: 39 mg. LC/MS purity (UV/MS): 100/90%, Rt 6.22 min. M+1: 243

Workup

  1. washThe organic phase was washed with saturated NaHCO3 (3×10 mL), dried Na2SO4
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72242455545b499ba3bfa33ff5185577
Source dataset
uspto-grants-2010_11
Patent number
US07825265B2

Reaction notes

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