4-Bromo-1,2-dichlorobenzene → HCID 66687908, compound

HRID 1895008Notes

Reaction equation

HRID 1895008 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27](=[O:32])N(OC)C)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([C:27](=[O:32])[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 66687908HCID 66687908, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

tert-Butyllithium (1.7 M in pentane, 2.5 mL, 4.25 mmol) was added at −78° C. to a solution of 4-bromo-1,2-dichlorobenzene (435 mg, 1.93 mmol) in THF (10 mL) under nitrogen atmosphere. The resulting solution was stirred at −78° C. for 15 minutes, and then a solution of 3-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 1.93 mmol) in THF (2 mL) was slowly added. The reaction mixture was stirred at −78° C. for 20 minutes and then warmed up to room temperature over a period of 30 minutes. The reaction was quenched by addition of saturated aqueous NH4Cl, then diluted with water and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure to give an oil that was purified by flash chromatography (10% to 30% of EtOAc in hexane) to give 143 mg (22% yield) of 3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 20 minutes
  2. temperaturewarmed up to room temperature over a period of 30 minutes
  3. customThe reaction was quenched by addition of saturated aqueous NH4Cl
  4. additiondiluted with water
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give an oil that
  10. customwas purified by flash chromatography (10% to 30% of EtOAc in hexane)

Sources & evidence

ORD record
ord-628ada4ddfb747298a885134c84b1ece
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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