Sulfuric Acid → alpha-Ethenyl-2,3,5-trifluorobenzenemethanol

HRID 2395601ノート

反応式

HRID 2395601 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[F:10].C([Li])CCC.[CH:16]([CH:18]=[CH2:19])=[O:17].OS(O)(=O)=O>CCOCC.CCCCCC>[CH:18]([CH:16]([C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[F:10])[OH:17])=[CH2:19]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 7847AcroleinHCID 27363991-Bromo-2,3,5-trifluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 18989434alpha-Ethenyl-2,3,5-trifluorobenzenemethanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-73 °C

実験手順

A solution of 4.1 g (0.0194 mol) of 1-bromo-2,3,5-trifluorobenzene in 50 ml of anhydrous ether is cooled to -76 ° C. under a nitrogen atmosphere. 12.1 ml (0.0194 mol) of a 1.6M solution of n-butyllithium in hexane are added dropwise over 15 minutes at a temperature below -72° C. The mixture is stirred for 2 minutes at -73° C. and then a solution of 1.15 g (0.0205 mol) of acrolein in 5 ml of anhydrous ether is added dropwise. The mixture is stirred for 30 minutes at -70° C. and is then allowed to return to room temperature. The mixture is poured onto a mixture of 100 g of ice and 10 g of concentrated H2SO4. Extraction with ether, washing with water, drying over Na2SO4, filtration and concentration under vacuum are carried out. The residue obtained is used without other purification in the following stage. Weight obtained: 3.1 g (Yd.=86%)

後処理

  1. stirringThe mixture is stirred for 30 minutes at -70° C.
  2. customto return to room temperature
  3. extractionExtraction with ether
  4. washwashing with water
  5. dry with materialdrying over Na2SO4, filtration and concentration under vacuum
  6. customThe residue obtained
  7. customis used without other purification in the following stage
  8. customWeight obtained

出典と根拠

ORDレコード
ord-6aa5a469fe3a48d68201a3035910c5b9
出典データセット
uspto-grants-1996_02
特許番号
US05489592

反応ノート

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