Water → [4-(3,5-Bis(4-trifluoromethylphenyl)-benzyloxy)-2-methyl-phenoxy]-acetic acid methyl ester

HRID 19501

反応式

HRID 19501 の反応式
[CH3:1][O:2][C:3](=[O:23])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[C:18](Br)[CH:17]=[C:16](Br)[CH:15]=2)=[CH:8][C:7]=1[CH3:22].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1(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)C=CC=CC=1.C(O)C>[CH3:1][O:2][C:3](=[O:23])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[C:18]([C:29]3[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=3)[CH:17]=[C:16]([C:29]3[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=3)[CH:15]=2)=[CH:8][C:7]=1[CH3:22]

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 59007639[4-(3,5-Dibromo-benzyloxy)-2-methyl-phenoxy]-acetic acid methyl ester

生成物 1

HCID 59007659[4-(3,5-Bis(4-trifluoromethylphenyl)-benzyloxy)-2-methyl-phenoxy]-acetic acid methyl ester

試薬・触媒・溶媒 3

HCID 178420554HCID 178420554、化合物触媒HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

[4-(3,5-Dibromo-benzyloxy)-2-methyl-phenoxy]-acetic acid methyl ester 13 (0.0375 g, 0.088 mmol) is dissolved in dioxane (1 mL). 4-Trifluoromethyl-phenylboronic acid (0.0514 g, 0.27 mmol) is added, followed by water (0.01 mL), ethanol (0.01 mL), potassium carbonate (0.0557 g, 0.4 mmol), and tetrakis-(triphenylphosphino)palladium (0.117 g, 0.01 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 10 min). The resulting orange suspension is filtered, the solids are washed with more dioxane, and the resulting solution is concentrated and purified by silica gel chromatography (10% to 25% ethyl acetate in hexanes) to yield [4-(3,5-bis(4-trifluoromethylphenyl)-benzyloxy)-2-methyl-phenoxy]-acetic acid methyl ester as an oil. 1H-NMR (400 MHz, CDCl3) δ=7.77-7.64 (m, 8H), 7.52 (s, 2H), 7.34 (s, 1H), 6.88 (d, J=2.8 Hz, 1H), 6.76 (dd, J=9.0, 2.8 Hz, 1H), 6.68 (d, J=9.2 Hz, 1H), 5.14 (s, 2H), 4.61 (s, 2H), 3.80 (s, 3H), 2.95 (s, 3H). 19F-NMR (376 MHz, CDCl3) δ=−62.4.

後処理

  1. custom(170° C. for 10 min)
  2. filtrationThe resulting orange suspension is filtered
  3. washthe solids are washed with more dioxane
  4. concentrationthe resulting solution is concentrated
  5. custompurified by silica gel chromatography (10% to 25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-7a832f42aae44ab2a68129c86662f279
出典データセット
uspto-grants-2010_06
特許番号
US07745445B2

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