Diethyl Ether → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

HRID 40276Notes

Reaction equation

HRID 40276 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([Cl:14])[CH:3]=1.[CH3:15][Mg]Br.C(OCC)C>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH3:15])=[C:4]([Cl:14])[CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 598430764-bromo-2-chloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (890 mg, 3195 μmol) in THF (10 mL) at −5° C. under nitrogen was slowly added methylmagnesium bromide 3.0 m in diethyl ether (1278 μl, 3834 μmol). After 30 min another 1.3 mL (3.8 mmol; 1.2 eq) of MeMgBr added at 23° C. After an additional hour, LCMS suggests 95% conversion. Reaction quenched with sat NH4Cl (10 mL) and resulting white cake washed repeatedly with diethyl ether. Combined organics washed with water and sat NaCl then pushed through a plug of silica (10 g). 1-(4-bromo-2-chlorophenyl)ethanone isolated as a colorless oil.

Workup

  1. customat −5° C.
  2. waitAfter an additional hour
  3. customReaction
  4. customquenched with sat NH4Cl (10 mL)
  5. customresulting white cake
  6. washwashed repeatedly with diethyl ether
  7. washCombined organics washed with water

Sources & evidence

ORD record
ord-a930d2c325954dec9486a4741f317562
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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