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

HRID 1439043노트

반응식

HRID 1439043 반응식
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

참가 물질

10

반응물 6

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매3회HCID 24485Mercuric Iodide촉매HCID 8028Tetrahydrofuran용매4회

실험 절차

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°.

후처리

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

출처 및 근거

ORD 기록
ord-9e120e94955749679e8839c788553997
출처 데이터셋
uspto-grants-1977_11
특허 번호
US04057647

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