Potassium Carbonate → 6-Fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester

HRID 457977노트

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HRID 457977 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8](Br)[C:7]([F:11])=[CH:6][C:5]=1[O:12][CH3:13].C([O-])([O-])=O.[K+].[K+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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.OO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]([F:11])=[CH:6][C:5]=1[O:12][CH3:13])=[O:14]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 22093493Methyl 5-bromo-4-fluoro-2-methoxybenzoate

생성물 1

HCID 220934916-Fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester수율 91%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 784Hydrogen Peroxide용매

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온도
110 °C

실험 절차

To a flame dried flask containing degassed toluene (15.2 mL, 0.5 M) was added 5-bromo-4-fluoro-2-methoxy-benzoic acid methyl ester (2.0 g, 7.6 mmol), anhydrous K2CO3 (2.1 g, 15.2 mmol), phenylboronic acid (3.7 g, 30.4 mmol), and Pd(PPh3)4 (0.88 g, 0.76 mmol). Using a reflux condenser, the stirring mixture was heated to 110° C. for 3.5 h. The mixture was then cooled to room temperature, placed in an ice bath and H2O2 (30%, 10 mL) was slowly added. The ice bath was removed and the reaction was allowed to stir at room temperature for one hour. The mixture was then diluted with ether and washed successively with 2 N HCl and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated to afford a brown oil. Purification by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min) provided 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester (1.8 g, 91%) as a pale yellow solid: Rf 0.5 (40% ethyl acetate in heptane);

후처리

  1. customTo a flame dried flask
  2. additioncontaining
  3. customdegassed toluene (15.2 mL, 0.5 M)
  4. temperatureThe mixture was then cooled to room temperature
  5. customplaced in an ice bath
  6. customThe ice bath was removed
  7. additionThe mixture was then diluted with ether
  8. washwashed successively with 2 N HCl and saturated aq NaCl
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto afford a brown oil
  13. customPurification by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min)

출처 및 근거

ORD 기록
ord-b94396d1f5c24e158e0380c991d078ca
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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