Potassium Carbonate → HCID 803776, compound

HRID 1916549Notes

Reaction equation

HRID 1916549 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([Cl:24])[CH:18]=1>CN(C=O)C.CCOC(C)=O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:19]([Cl:24])[CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 803776HCID 803776, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

415 mg (3.00 mmol) K2CO3 and 170 mg (1.00 mmol) N-(2-chloroethyl)-pyrrolidine-hydrochloride is added to a solution of 207 mg (1.00 mmol) 4-bromo-2-chloro-phenol in 5 mL DMF and the mixture is stirred for 24 h at RT. The reaction mixture is diluted with 50 mL EtOAc, extracted once with 30 mL water and twice with 30 mL semisaturated NaHCO3 solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 9:1).

Workup

  1. extractionextracted once with 30 mL water and twice with 30 mL
  2. dry with materialThe organic phase is dried over MgSO4
  3. customFurther purification

Sources & evidence

ORD record
ord-b18d3f4d4e944687b1b188b6de885fc9
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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