Acetyl chloride → 3-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

HRID 26899

反応式

HRID 26899 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].FC1C=C(F)C=CC=1C1C=CC=CC=1.C(Cl)(=O)C.[Al+3].[Cl-].[Cl-].[Cl-].Br[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[CH:6][CH:5]=1)([OH:3])[CH3:2])[CH3:46]

参加物

8

反応物 5

HCID 6367Acetyl chlorideHCID 7748Ethyl bromoacetateHCID 1045421-(2',4'-Difluoro(1,1'-biphenyl)-4-yl)ethan-1-oneHCID 1699742,4-Difluoro-1,1'-biphenylHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 538342513-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 1140Toluene溶媒

実験手順

23.2 g. of 4-acetyl-2',4'-difluorobiphenyl, obtainable by reacting 2,4-difluorobiphenyl with acetyl chloride in the presence of AlCl3, and 11.1 ml. of ethyl bromoacetate are dissolved in a mixture of 75 ml. of benzene and 75 ml. of toluene. A 40 ml. portion of the resulting solution is added to 7 g. of zinc powder, previously washed successively with 1% hydrochloric acid, water and acetone and dried and the mixture is warmed to 70° with stirring and under a nitrogen atmosphere. After the reaction has begun, the remainder of the solution is added dropwise, the mixture is heated under reflux for one hour and cooled and 40 ml. of 20% sulfuric acid are added drop-wise in order to decompose the alcoholate Z--C(CH3) (OZnBr)--CH2 --COOC2H5 (Z is 2',4'-difluoro-4-biphenylyl). The organic phase is separated off and worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester, m.p. 96°-97° C.

後処理

  1. additionportion of the resulting solution is added to 7 g
  2. washof zinc powder, previously washed successively with 1% hydrochloric acid, water and acetone
  3. customdried
  4. temperaturethe mixture is warmed to 70°
  5. additionthe remainder of the solution is added dropwise
  6. temperaturethe mixture is heated
  7. temperatureunder reflux for one hour
  8. temperaturecooled
  9. additionof 20% sulfuric acid are added drop-wise in order
  10. customThe organic phase is separated off

出典と根拠

ORDレコード
ord-e10f69b05c2e4c25830c03c54053918b
出典データセット
uspto-grants-1979_04
特許番号
US04151302

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