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

HRID 19501

반응식

HRID 19501 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178420554HCID 178420554, 화합물촉매HCID 702Ethanol용매HCID 312751,4-Dioxane용매

실험 절차

[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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7a832f42aae44ab2a68129c86662f279
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745445B2

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