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Potassium Carbonate → 2-Fluoro-5-(3-fluorophenyl)-3-methyl-benzoic acid

HRID 1771622
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HRID 1771622 반응식
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>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.O>[F:11][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 814779685-Bromo-2-fluoro-3-methylbenzoic acid

생성물 1

HCID 894436582-Fluoro-5-(3-fluorophenyl)-3-methyl-benzoic acid수율 75.2%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 962Water용매

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온도
85 °C

실험 절차

To a solution of 5-bromo-2-fluoro-3-methyl-benzoic acid (697 mg, 2.99 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (502 mg, 3.59 mmol, 1.2 eq) in a mixture of EtOH (10 mL), dioxane (20 mL) and H2O (10 mL) were added K2CO3 (142 mg, 1.03 mmol, 2.5 eq) and Pd(PPh3)4 (345 mg, 0.30 mmol, 0.1 eq). The mixture was heated at 85° C. overnight. The reaction was quenched by addition of 1M HCl and the aqueous phase extracted with EtOAc. The organic extract was dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography to give the title compound as a solid (558 mg, 73%).

후처리

  1. customThe reaction was quenched by addition of 1M HCl
  2. extractionthe aqueous phase extracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-3c288aa163a147aba797e6b333fa82bc
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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