Boron tribromide → 3-[4-(5-Hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

HRID 1822344노트

반응식

HRID 1822344 반응식
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 578941493-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

생성물 1

HCID 578941473-[4-(5-Hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound of 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (1.02 g, 3.10 mmol) is dissolved in DCM (15 mL) under nitrogen at −78° C., and BBr3 (1M, CH2Cl2) (4.64 mL, 4.64 mmol) is added. The mixture is stirred at that temperature for 10 minutes and the bath is removed. The mixture is stirred at rt for 2 h, and water is added. The mixture is neutralized to pH=7 with NaOH (10%). The mixture is extracted with DCM. The organic layer is dried with Na2SO4 and filtered, and then the solvent is evaporated in vacuo. Purification by flash chromatography by eluting with hexane:ethyl acetate 5:1 to afford the title compound (0.48 g, 50%). Rf=0.13 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.26 (t, 3H, J=7.3 Hz), 2.16 (s, 3H), 2.26 (s, 3H), 2.57 (t, 2H, J=7.3 Hz), 2.89 (t, 2H, J=7.5 Hz), 4.15 (q, 2H, J=7.3 Hz), 6.44 (d, 1H, J=2.4 Hz), 6.58 (dd, 1H, J=2.4, 8.1 Hz), 6.68 (dd, 1H, J=2.4, 8.3 Hz), 6.75 (d, 1H, J=2.2 Hz), 6.92 (s, 1H), 7.04 (t, 2H, J=8.1 Hz).

후처리

  1. customthe bath is removed
  2. stirringThe mixture is stirred at rt for 2 h
  3. additionwater is added
  4. extractionThe mixture is extracted with DCM
  5. dry with materialThe organic layer is dried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent is evaporated in vacuo
  8. customPurification by flash chromatography
  9. washby eluting with hexane:ethyl acetate 5:1

출처 및 근거

ORD 기록
ord-9f817ed0467e4f548bd8971a13029a30
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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