Dichloromethane → HCID 66968119, compound

HRID 70740

Reaction equation

HRID 70740 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 66968119HCID 66968119, compound

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-7c2b84a7b779425e99164e43cf496820
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Linked notes

Loading…