Hydrochloric Acid → 1-(3-Fluoro-4-isopropoxyphenyl)ethanone

HRID 1690166Notes

Reaction equation

HRID 1690166 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5](N(OC)C)=[O:6].[CH3:18][Mg]Br.O.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:18])[CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 866394073-Fluoro-4-(1-methylethoxy)-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 284145381-(3-Fluoro-4-isopropoxyphenyl)ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-fluoro-4-(1-methylethoxy)-N-methoxy-N-methylbenzamide (117 mg, 0.485 mmol) in tetrahydrofuran (2.4 mL), methylmagnesium bromide (750 μL, 0.728 mmol) was added under ice-cold conditions, and the resultant mixture was stirred for 1 hour under ice-cold conditions. The reaction solution was added with water and 5% aqueous solution of hydrochloric acid under ice-cold conditions, and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 1-(3-Fluoro-4-(1-methylethoxy)phenyl)ethanone (94 mg, yield 99%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-686b4eda188847dc9de518ea42ed506d
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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