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Water → 1-Fluoro-5-(3-fluorophenyl)-2-methyl-3-nitro-benzene

HRID 1771726
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인쇄 미리보기

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HRID 1771726 반응식
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCO.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>[F:8][C:6]1[CH:7]=[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[CH3:9]
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참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 27733874-Bromo-2-fluoro-6-nitrotoluene

생성물 1

HCID 894454551-Fluoro-5-(3-fluorophenyl)-2-methyl-3-nitro-benzene수율 75.3%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of 5-bromo-1-fluoro-2-methyl-3-nitro-benzene (5.0 g, 21.31 mmol, 1.0 eq), 3-fluorophenylboronic acid (3.29 g, 23.8 mmol, 1.1 eq), Pd(PPh3)4 (1.2 g, 1.07 mmol, 0.05 eq) and K2CO3 (11.8 g, 85.5 mmol, 4 eq) in a mixture of dioxane (150 mL) and EtOH (50 mL) was heated at 80° C. under N2 overnight. After cooling to room temperature the reaction was poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as an oil (4.0 g, 75%). This material was used without further purification.

후처리

  1. temperatureAfter cooling to room temperature the reaction
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-8932958eee904939b83aefc6c399378f
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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