Hydrochloric Acid → HCID 14770832、化合物

HRID 1090378ノート

反応式

HRID 1090378 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.C([O:18][C:19]1[CH2:23][CH2:22][C:21](=O)[CH:20]=1)C.Cl>CCOCC>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:21]2[CH2:22][CH2:23][C:19](=[O:18])[CH:20]=2)=[C:3]([F:10])[CH:4]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418339Butyllithium

生成物 1

HCID 14770832HCID 14770832、化合物収率 52%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

A solution of 27.2 g (0.1 mole) of 1,4-dibromo-2,5-difluorobenzene in 200 ml of ether was blanketed with argon and cooled to -78° C. To this mixture was added 42 ml of n-butyl lithium (2.4 M; 0.10 mole) dropwise via an addition funnel. The solution was stirred at -78° C. for 15 minutes, then allowed to warm to -45° C. To the anion was added 13 ml of 3-ethoxy-2-cyclopentenone (0.10 mole); the solution was kept at -45° for 30 minutes and was then warmed slowly to room temperature. The mixture was poured into 250 ml of 1 N hydrochloric acid, stirred for 30 minutes, and extracted with ethyl acetate; the organic phases were combined, washed with water, dried over magnesium sulfate, and concentrated. The crude product was purified via silica gel chromatography using an 80:20 chloroform ethyl acetate mixture to give 14.2 g of the desired product; mp 129°-131° C.

後処理

  1. temperatureto warm to -45° C
  2. waitthe solution was kept at -45° for 30 minutes
  3. temperaturewas then warmed slowly to room temperature
  4. stirringstirred for 30 minutes
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-c6fc12634cad495a8fa5ff8a8c62d925
出典データセット
uspto-grants-1992_01
特許番号
US05081254

反応ノート

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