Hydrochloric Acid → 2-Fluoro-3-(3-fluorophenyl)-5-methyl-benzoic acid

HRID 1771617노트

반응식

HRID 1771617 반응식
Br[C:2]1[C:3]([F:12])=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[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+].Cl>C(#N)C.O.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:12][C:3]1[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][C:9]([CH3:11])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 125134713-Bromo-2-fluoro-5-methylbenzoic acid

생성물 1

HCID 894435072-Fluoro-3-(3-fluorophenyl)-5-methyl-benzoic acid수율 75%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-bromo-2-fluoro-5-methyl-benzoic acid (400 mg, 1.7 mmol, 1.0 eq), (3-fluorophenyl)boronic acid (720 mg, 5.2 mmol, 3.0 eq), K2CO3 (356 mg, 2.6 mmol, 1.5 eq) and Pd(PPh3)4 (396.0 mg, 0.40 mmol, 0.2 eq) in acetonitrile (5 mL) and H2O (4 mL) was heated at reflux overnight. The reaction was acidified to pH 3 by addition of 1M HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as a solid (160 mg, 75%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

출처 및 근거

ORD 기록
ord-19e6800bfa664814815290fed911bfe5
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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