Acetic Acid → 2',3'-Difluoro-4'-(1-hydroxyethyl)-acetanilide

HRID 1607192노트

반응식

HRID 1607192 반응식
[F:1][C:2]1[C:11]([F:12])=[C:10]([CH:13]=[O:14])[CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].C[Mg+].[Br-].[CH3:18]C(O)=O>C1COCC1>[F:1][C:2]1[C:11]([F:12])=[C:10]([CH:13]([OH:14])[CH3:18])[CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 146210402',3'-Difluoro-4'-formylacetanilideHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 198531742',3'-Difluoro-4'-(1-hydroxyethyl)-acetanilide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
15 °C

실험 절차

To a stirred solution of 7.7 g of 2',3'-difluoro-4'-formylacetanilide in 190 mL of THF under an N2 atmosphere is added 29 mL of a 2.85M solution of MeMgBr at a temperature of 10°-20° C. The thick suspension is stirred 20 minutes at 20°-25° C., cooled to 15° C. and 5 mL of AcOH cautiously added. The mixture is then poured onto 500 mL of ice/H2O and the product extracted into 500 mL of CH2CL2. This extract is washed with H2O, saturated NaHCO3 and H2O (100 mL each) and stripped to give 8.1 g of yellow gummy 2',3'-difluoro-4'-(1-hydroxyethyl)-acetanilide. 8.1 g of the crude 2',3'-difluoro-4'-(1-hydroxyethyl)-acetanilide is stirred in acetone (175 mL) while 54 mL of Kilianis' reagent (Fieser and Fieser, "Reagents for Organic Synthesis", Vol. I p144) is added dropwise during 30 min. at a temperature of 20°-25° C. After stirring 30 min. longer, the reaction mixture is poured onto 200 mL of ice/H2O containing 5 g of Na2S2O5. The green suspension is extracted three times with CH2Cl2 (total volume 1 L) and the organic extract is washed with H2O, saturated NaHCO3, H2O (100 mL each) and stripped in vacuo. There is obtained 5.8 g of off-white solid which is slurried with 75 mL of Et2O to afford 5.23 g (65% yield) of 4'-acetyl-2',3'-difluoroacetanilide, m.p. 149°-152° C., (Mass spectrum shows an ion of 214).

후처리

  1. extractionthe product extracted into 500 mL of CH2CL2
  2. washThis extract is washed with H2O, saturated NaHCO3 and H2O (100 mL each)

출처 및 근거

ORD 기록
ord-2af8e1e3607545cc818a9ed3a5d7e302
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863959

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