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Sodium Carbonate → 3',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid

HRID 1771586
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인쇄 미리보기

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HRID 1771586 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CCO.CN(C=O)C.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:11][C:5]1[CH:4]=[CH:3][C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]
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참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 27363155-Bromo-2-fluorobenzoic acid

생성물 1

HCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid수율 97%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매
HCID 702
Ethanol
용매
HCID 962Water용매2회
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a mixture of 5-bromo-2-fluorobenzoic acid (3 g, 13.2 mmol, 1.0 eq) and 3-fluorophenyl boronic acid (2.1 g, 15.1 mmol, 1.1 eq) in water (15 mL), EtOH (15 mL) and DMF (60 mL) was added Na2CO3 (5.81 g, 54.8 mmol, 4.1 eq) and Pd(PPh3)4 (1.58 g, 1.37 mmol, 0.1 eq). The reaction mixture was heated at 100° C. under nitrogen for 4 h, then cooled to room temperature. The resulting mixture was poured into water and extracted with ethyl acetate. The organic extracts were combined, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white powder (3 g, 97%).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-4dd1889d74ea40199768310501908119
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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