Boron tribromide → HCID 57894169, 화합물

HRID 1822303노트

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HRID 1822303 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]=[C:16]([F:22])[CH:15]=2)=[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]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 57894216HCID 57894216, 화합물

생성물 1

HCID 57894169HCID 57894169, 화합물수율 81.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A −78° C. solution of 3-[4-(3-fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.715 g, 2.15 mmol) in dry CH2Cl2 (10 mL) is treated with a 1 M CH2Cl2 solution of boron tribromide (6.5 mL, 6.5 mmol). The mixture is warmed to 0° C. and stirred for 1 hour under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 0.558 g (81%) of the title compound. Rf=0.36 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3). MS (ES−) m/z mass calculated for C18H19O4F 318, found 317 (M−1, 100%).

후처리

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-5bb0fdceeec84eecb0d1953dfb5fc5e7
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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