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

HRID 1993008ノート

反応式

HRID 1993008 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178420553HCID 178420553、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8cb530d40a464f5baaa9a51492e9b366
出典データセット
uspto-grants-2010_01
特許番号
US07649093B2

反応ノート

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