HCID 86028266, compound → 1-(3-Bromo-2-chlorophenyl)ethanone

HRID 1508174Notes

Reaction equation

HRID 1508174 reaction equation
[Br:1][C:2]1[C:3]([Cl:14])=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5](N(OC)C)=[O:6].[CH3:15][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[C:3]([Cl:14])=[C:4]([C:5](=[O:6])[CH3:15])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 86028266HCID 86028266, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 149373601-(3-Bromo-2-chlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-chloro-N-methoxy-N-methylbenzamide (0.71 mmol) in 7 mL THF was added a solution of MeMgBr (4.31 mmol, 3M solution in Et2O) at 0° C. The cooling bath was removed after 1 h and stirring was continued at RT overnight. The reaction was quenched with water and sat. aq. NH4Cl solution under cooling. The mixture was extracted with EtOAc (3×), the combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (85/15) gives the desired compound as colorless oil;

Workup

  1. customThe cooling bath was removed after 1 h
  2. customThe reaction was quenched with water and sat. aq. NH4Cl solution
  3. temperatureunder cooling
  4. extractionThe mixture was extracted with EtOAc (3×)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-5718639eb61448cbaa419fd582f79223
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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