Hydrochloric Acid → 2-Fluorobenzofuran-5-carbaldehyde

HRID 2108711ノート

反応式

HRID 2108711 の反応式
[Mg].II.Br[C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([F:13])=[CH:10][C:9]=2[CH:14]=1.Cl.[O:16]1CCC[CH2:17]1>[Cl-].[Na+].O.CN(C)C=O>[F:13][C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([CH:17]=[O:16])=[CH:14][C:9]=2[CH:10]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028Tetrahydrofuran2 回HCID 5462224MagnesiumHCID 574391135-Bromo-2-fluoro-1-benzofuran

生成物 1

HCID 450908312-Fluorobenzofuran-5-carbaldehyde

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A slurry of magnesium powder (219 mg) and iodine (cat) in dry tetrahydrofuran (3 ml) was heated at 50° C. under nitrogen for 20 minutes. 5-Bromo-2-fluoro-1-benzofuran (1.4 g) was dissolved in dry tetrahydrofuran (6 ml). A 1 ml portion of the solution was added to the slurry at 50° C. without stirring. After 30 minutes the rest of the solution was added slowly and the reaction was heated at reflux for 3 hours. The reaction was cooled in an ice/water bath and dimethylformamide (1 ml) was added dropwise maintaining the temperature below 10° C. After 1 hour a mixture of 2N hydrochloric acid (12.5 ml) and brine (12.5 ml) was added. The reaction mixture was extracted using ethyl acetate (3×25 ml). The combined organics were washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue applied to a silica cartridge (50 g). This was eluted with cyclohexane, cyclohexane/ethyl acetate (6:1, 5:1 v/v). This gave 2-fluoro-5-formyl-1-benzofuran (376 mg).

後処理

  1. additionA 1 ml portion of the solution was added to the slurry at 50° C.
  2. additionAfter 30 minutes the rest of the solution was added slowly
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 3 hours
  5. temperatureThe reaction was cooled in an ice/water bath
  6. temperaturemaintaining the temperature below 10° C
  7. additionwas added
  8. extractionThe reaction mixture was extracted
  9. washThe combined organics were washed with brine
  10. dry with materialdried over anhydrous magnesium sulphate
  11. customThe solvent was removed in vacuo
  12. washThis was eluted with cyclohexane, cyclohexane/ethyl acetate (6:1, 5:1 v/v)

出典と根拠

ORDレコード
ord-53849f3ae6794609b1e0232446cc8194
出典データセット
uspto-grants-2009_04
特許番号
US07514437B2

反応ノート

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