Water → Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-

HRID 1774531ノート

反応式

HRID 1774531 の反応式
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[F:17][CH:13]([F:18])[O:11][C:4]1[CH:3]=[C:2]([F:1])[C:7]([CH2:8][OH:9])=[C:6]([F:10])[CH:5]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

生成物 1

HCID 69140944Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-収率 56%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

500 mg 3,5-difluoro-4-(hydroxymethyl)phenol (3.12 mmol, 1.0 eq.) were dissolved in DMF. 523 mg sodium chloro(difluoro)acetate (3.44 mmol, 1.1 eq.), 1.22 g cesium carbonate (3.75 mmo, 1.2 eq) and 0.20 mL water (10.9 mmol, 3.5 eq.) were added. The reaction mixture was stirred at 100° C. over night. The reaction mixture was divided between water and ethyl acetate. The aqueous layer was washed twice with ethyl acetate. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo. The crude product was purified by flash chromatography to provide 161 mg (0.69 mmol, 22%) of the 56% pure target compound.

後処理

  1. washThe aqueous layer was washed twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried over a silicon
  4. filtrationfilter
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-102bcce275ce46c19256eec05eec3aeb
出典データセット
uspto-grants-2016_02
特許番号
US09260412B2

反応ノート

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