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Sodium Hydroxide → 1-Bromo-3-difluoromethoxy-5-vinylbenzene

HRID 1717482
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인쇄 미리보기

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HRID 1717482 반응식
[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.Br[C:17]1[CH:22]=[C:21]([O:23][CH:24]([F:26])[F:25])[CH:20]=[C:19]([Br:27])[CH:18]=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:27][C:19]1[CH:18]=[C:17]([CH:1]=[CH2:2])[CH:22]=[C:21]([O:23][CH:24]([F:26])[F:25])[CH:20]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 219046401,3-Dibromo-5-(difluoromethoxy)benzeneHCID 53438229Tri(butyl)vinyltin

생성물 1

HCID 219046371-Bromo-3-difluoromethoxy-5-vinylbenzene수율 68%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매

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온도
50 °C

실험 절차

Tri(butyl)vinyltin (10.5 g, 33.1 mmol) was added dropwise to a solution of 1,3-dibromo-5-difluoromethoxybenzene (9.1 g, 30.1 mmol; see step (i) above), tetrakis(triphenylphosphine)palladium(0) (700 mg, 0.60 mmol), and 2,6-di-tert-butyl-4-methylphenol (spatula tip) in toluene (125 mL) under nitrogen. The mixture was stirred at 50° C. overnight. The mixture was cooled to 0° C. and 1N NaOH (70 mL) was added. After 1 h, the mixture was extracted with CH2Cl2 (3×300 mL) then, the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with hexanes afforded the sub-title compound (5.1 g, 68%) as a colourless oil.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. waitAfter 1 h
  3. extractionthe mixture was extracted with CH2Cl2 (3×300 mL)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d9d8530d459d4d7ebcfd29ee94cde082
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803954B2

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