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Potassium Carbonate → 4-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-methoxy-benzoic acid ethyl ester

HRID 1483651
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HRID 1483651 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]1[O:13][CH2:12][CH2:11][O:10]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[O:31][CH3:32])[CH3:21]>CS(C)=O.CCOC(C)=O>[CH2:20]([O:22][C:23](=[O:33])[C:24]1[CH:29]=[CH:28][C:27]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH:9]3[O:10][CH2:11][CH2:12][O:13]3)[CH:4]=2)=[CH:26][C:25]=1[O:31][CH3:32])[CH3:21]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 18920212HCID 18920212, 화합물HCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenol

생성물 1

HCID 579690074-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-methoxy-benzoic acid ethyl ester수율 35%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of compound 2 (9.27 g, 37.83 mmol) in DMSO (50 mL) was added potassium carbonate (15.68 g, 113.48 mmol). The resulting mixture was stirred at rt for 30 min. followed by addition of compound 5 (8.99 g, 45.39 mmol). The resulting mixture was heated at 120° C. O/N. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to give crude product, which was purified by column chromatography (silica gel, 10% EtOAc in hexane) to afford the title compound 6 (5.6 g, 35%) as a pale yellow solid. 1H NMR 400 MHz (CDCl3) δ:

후처리

  1. temperatureThe resulting mixture was heated at 120° C
  2. washwashed with water (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude product, which
  6. customwas purified by column chromatography (silica gel, 10% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-9d7e3aea31d94645aa44fb331b2bfffe
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09416146B2

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