Dimethyl Sulfoxide → Ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate

HRID 1876396

反応式

HRID 1876396 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.Br[C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([CH3:9])[CH:3]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 1362954-Fluoro-2-methylphenol

生成物 1

HCID 67405334Ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-fluoro-2-methylphenol (10 g, 79.28 mmol), ethyl 2-bromoisobutyrate (23.2 mL, 158.6 mmol), potassium carbonate (21.9 g, 158.6 mmol), and DMSO (80 mL) was stirred at room temperature for 72 hours. Water and ethyl acetate were added and the layers were separated. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (20%) to afford ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate. To a solution of ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate (13.3 g, 55.44 mmol) in tetrahydrofuran (40 mL) and methanol (10 mL) was added NaOH (6.66 g, 166.32 mmol) in water (14 mL) and stirred overnight. The volatiles were removed in vacuo and acidified with concentrated HCl. The milky white solution was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoic acid (658) as a yellow solid.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (20%)

出典と根拠

ORDレコード
ord-6d6bb607b02143e09086c6f024ef9b8e
出典データセット
uspto-grants-2012_11
特許番号
US08309600B2

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