Dimethylformamide → 2-Fluoro-4,6-dihydroxybenzaldehyde

HRID 1004316ノート

反応式

HRID 1004316 の反応式
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[OH:11][C:12]1[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([OH:18])[CH:17]=1>O>[OH:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([F:19])[C:13]=1[CH:3]=[O:4]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 126587785-Fluororesorcinol

生成物 1

HCID 220104032-Fluoro-4,6-dihydroxybenzaldehyde収率 27.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Dimethylformamide (12.7 g) was added to vigorously stirred phosphorous oxychloride (14.4 g) at 0° C. The reaction mixture was stirred at this temperature for 30 minutes, then 3,5-dihydroxyfluorobenzene (6 g) was added. The sticky red syrup was allowed to warm to room temperature and stirred for 2 hours, then left to stand for 14 hours. Water (100 ml) was added and the mixture extracted three times with ethyl acetate (100 ml). The combined organic extracts were washed with brine (100 ml), dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2, v/v). Fractions homogeneous in the required product were combined and evaporated to give an orange solid which was triturated with ethyl acetate to give the title compound (2 g) as a yellow solid.

後処理

  1. stirringstirred for 2 hours
  2. waitleft
  3. waitto stand for 14 hours
  4. extractionthe mixture extracted three times with ethyl acetate (100 ml)
  5. washThe combined organic extracts were washed with brine (100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2
  9. customevaporated
  10. customto give an orange solid which
  11. customwas triturated with ethyl acetate

出典と根拠

ORDレコード
ord-53da613a47ea48c2bfa223e4727ea800
出典データセット
uspto-grants-2000_04
特許番号
US06048893

反応ノート

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