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Carbon tetrabromide → 4-(Bromomethyl)-5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]isoxazole

HRID 1748153
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HRID 1748153 반응식
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20]O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:42]>ClCCl>[Br:42][CH2:20][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 669061975-Cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-4-isoxazolemethanol

생성물 1

HCID 669060924-(Bromomethyl)-5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]isoxazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Into a 100 mL round bottom flask was placed (5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)-methanol (4 g, 13.3 mmol), triphenylphosphine (5.6 g, 20 mmol, 1.5 equiv) and dichloromethane (40 mL). The mixture was stirred until completely dissolved, and then slowly cannulated dropwise into a stirring solution of carbon tetrabromide (6.6 g, 20 mmol, 1.5 eq) in dichloromethane (20 ml). The mixture was stirred for one hour and the solvent was then evaporated in vacuo. The crude residue was purified by silica gel chromatography using a 0-50% gradient of ethyl acetate/hexane. The desired product was obtained as a colorless oil. MS m/z 361.9/363.9 (M+1, Br79/Br81 isotope pattern).

후처리

  1. customInto a 100 mL round bottom flask was placed
  2. dissolutionuntil completely dissolved
  3. stirringThe mixture was stirred for one hour
  4. customthe solvent was then evaporated in vacuo
  5. customThe crude residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-857b145d9c454ffabe6ec7464900db02
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150568B2

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