Hydrochloric Acid → 4-Chloro-2-[3-hydroxy-5-(hydroxymethyl)phenoxy]benzonitrile

HRID 1178456ノート

反応式

HRID 1178456 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[C:13]([OH:15])[CH:14]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20](F)[CH:19]=1.Cl>CN(C=O)C.C(OCC)C.O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([O:15][C:13]2[CH:14]=[C:9]([CH2:8][OH:7])[CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:19]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 346613,5-Dihydroxybenzyl alcoholHCID 936554-Chloro-2-fluorobenzonitrile

生成物 1

HCID 219304194-Chloro-2-[3-hydroxy-5-(hydroxymethyl)phenoxy]benzonitrile収率 9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a stirred solution of cesium carbonate (11.62 g) in dry DMF (70 ml) was added 5-(hydroxymethyl)-1,3-benzenediol (5 g) followed by 4-chloro-2-fluorobenzonitrile (5 g). The mixture was then stirred and heated at 120° C. for 3 h. The cooled mixture was then poured into water (200 ml) and made acidic by the addition of 2M aqueous hydrochloric acid. The products were extracted into ethyl acetate (3×150 ml), and the combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml). The organic extract was collected, dried (MgSO4) and concentrated to dryness. Diethyl ether was added to the residue and the mixture filtered. The filtrate was concentrated to dryness and the residue purified by chromatography (silica, 70% diethyl ether/isohexane) to afford, after trituration with diethyl ether, the sub-title compound (800 mg).

後処理

  1. extractionThe products were extracted into ethyl acetate (3×150 ml)
  2. washthe combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml)
  3. extractionThe organic extract
  4. customwas collected
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. additionDiethyl ether was added to the residue
  8. filtrationthe mixture filtered
  9. concentrationThe filtrate was concentrated to dryness
  10. customthe residue purified by chromatography (silica, 70% diethyl ether/isohexane)
  11. customto afford

出典と根拠

ORDレコード
ord-6d847fa096ae4e7585431bc4e0ffd0dc
出典データセット
uspto-grants-2007_10
特許番号
US07276528B2

反応ノート

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