Sodium Carbonate → 2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthalene

HRID 1993008노트

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HRID 1993008 반응식
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P([Pd-4](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)C=CC=CC=1.COCCOC>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:2]2[C:11]([CH3:12])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=3)[C:3]=2[O:15][CH2:16][O:17][CH3:18])=[CH:24][CH:25]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

생성물 1

HCID 685374682-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-methyl-naphthalene수율 84.2%

시약·촉매·용매 2

HCID 178420553HCID 178420553, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
160 °C

실험 절차

2-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14) (2.00 g, 6.44 mmol), 3-fluorobenzeneboronic acid (1.80 g, 12.88 mmol), tetrakis(triphenylphosphino)palladium (0) (0.74 g, 0.64 mmol), 2 M sodium carbonate (60 mL) and ethylene glycol dimethyl ether (60 mL) were combined and heated in a sealed tube at 160° C. for 75 min. The reaction was cooled to room temperature and filtered through a celite pad with 100 mL each diethyl ether and water. The organic layer was washed with brine (100 mL), dried (Na2SO4) and concentrated to an orange viscous oil. The crude product was purified by column chromatography with 10% EtOAc/hexane to afford 1.77 g (84%) of the title compound, 283 as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 2.14 (s, 3H), 3.02 (s, 3H), 3.86 (s, 3H), 4.71 (s, 3H), 7.12-7.23 (m, 4H), 7.25 (d, J=2.5 Hz, 1H), 7.46-7.52 (m, 1H), 7.53 (s, 1H), 7.93 (d, J=9.2 Hz, 1H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through a celite pad with 100 mL each diethyl ether and water
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to an orange viscous oil
  6. customThe crude product was purified by column chromatography with 10% EtOAc/hexane

출처 및 근거

ORD 기록
ord-8cb530d40a464f5baaa9a51492e9b366
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

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