Hydrochloric Acid → 1-(2-Bromo-5-chlorophenyl)ethanone

HRID 1743951

Reaction equation

HRID 1743951 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](N(OC)C)=[O:8].Cl.O>O1CCCC1>[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](=[O:8])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 222365462-Bromo-5-chloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 124866171-(2-Bromo-5-chlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methylmagnesium bromide (4.26 mL of a 1.4M solution in tetrahydrofuran/toulene, 5.97 mmol) was added dropwise to a stirred solution of 2-bromo-5-chloro-N-methoxy-N-methylbenzamide (0.554 g, 1.99 mmol) in tetrahydrofuran (20 mL) at approximatately 0° C. After 1 h, 1N hydrochloric acid (5 mL) was added and the resulting biphasic mixture was stirred vigorously for about 10 min. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0–10% ethyl acetate/hexanes as eluent) provided the title compound as a colorless oil.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0–10% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-eaae6ffbaf81461ab44aa2a09e09c742
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Linked notes

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