Hydrochloric Acid → 3-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid

HRID 1439043ノート

反応式

HRID 1439043 の反応式
Br[CH2:2][C:3]([OH:5])=[O:4].[Br-].C([Zn+])C=C.C(Br)C=C.[C:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[Na+].[Br-].Cl>C1COCC1.[Zn].[Hg](I)I>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([C:15]([OH:17])([CH3:16])[CH2:2][C:3]([OH:5])=[O:4])=[CH:19][CH:20]=1

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 7841Allyl bromideHCID 1045421-(2',4'-Difluoro(1,1'-biphenyl)-4-yl)ethan-1-oneHCID 253881Sodium BromideHCID 178455868HCID 178455868、化合物

生成物 1

HCID 213225833-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid

試薬・触媒・溶媒 3

HCID 23994Zinc触媒3 回HCID 24485Mercuric Iodide触媒HCID 8028Tetrahydrofuran溶媒4 回

実験手順

A solution of 12.9 g. of bromoacetic acid in 50 ml. of THF is added slowly dropwise at 10°-15° to a solution of 19 g. of allyl-zinc bromide in 200 ml. of THF, prepared by reacting allyl bromide with zinc filings in THF. A solution of 23.2 g. of 4-acetyl-2',4'-difluorobiphenyl in 100 ml. of THF, 6.5 g. of zinc filings, 100 mg. of HgI2 and 10.3 g. of NaBr are added to the reaction mixture, which contains an intermediate of the formula BrCH2 -COOZnBr, and heated under reflux until all the zinc has dissolved. After the alcholate formed has been decomposed with dilute hydrochloric acid, the mixture is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid, m.p. 121°-123°.

後処理

  1. temperatureheated
  2. dissolutionhas dissolved
  3. customAfter the alcholate formed

出典と根拠

ORDレコード
ord-9e120e94955749679e8839c788553997
出典データセット
uspto-grants-1977_11
特許番号
US04057647

反応ノート

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