1,1-Dichloroethane → HCID 66816707, compound

HRID 1755000Notes

Reaction equation

HRID 1755000 reaction equation
ClC(Cl)C.[Br:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]([CH2:18][CH:19](OCC)OCC)[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][C:7]=1[CH3:26].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:5][C:6]1[C:11]([CH3:12])=[C:10]2[C:9](=[CH:8][C:7]=1[CH3:26])[N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:18]=[CH:19]2

Participants

6

Reactant 3

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 66817773HCID 66817773, compound

Product 1

HCID 66816707HCID 66816707, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 1 M solution of titanium(IV) chloride in dichloroethane (5.3 ml, 5.3 mmol) was added to a solution of N-(4-bromo-3,5-dimethyl-phenyl)-N-(2,2-diethoxy-ethyl)-methanesulfonamide (2.09 g, 5.3 mmol) in toluene (17 ml) at room temperature, and the mixture was heated with stirring at 100° C. for two hours. An aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 5-bromo-4,6-dimethyl-1-methanesulfonyl-indole (1.28 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic phase was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1f15e4c502d04c4ab962ed4a1d76a6c3
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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