Cesium carbonate → 4-Bromo-1-chloro-2-(4-(2-cyclopropoxyethoxy)benzyl)benzene

HRID 425100노트

반응식

HRID 425100 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S(O[CH2:34][CH2:35][O:36][CH:37]2[CH2:39][CH2:38]2)(=O)=O)=CC=1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:34][CH2:35][O:36][CH:37]3[CH2:39][CH2:38]3)=[CH:10][CH:9]=2)[CH:15]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenolHCID 59557773Toluene-4-sulfonic acid 2-cyclopropoxy-ethyl ester

생성물 1

HCID 595577554-Bromo-1-chloro-2-(4-(2-cyclopropoxyethoxy)benzyl)benzene수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(5-bromo-2-chlorobenzyl)phenol (56.7 g, 210 mmol) and Cs2CO3 (135 g, 420 mmol) in DMF (350 mL) was stirred at room temperature for 30 min, and then 2-cyclopropoxyethyl 4-methylbenzenesulfonate (crude intermediate BP from the second preceeding step above) (53.3 g, 210 mmol) was added. The reaction mixture was stirred at room temperature overnight, and then diluted with water (3 L) and extracted with EtOAc. The organic layer was washed with water, then with brine, and dried over Na2SO4. The residue was concentrated and then purified by flash column chromatography on silica gel (eluent PE:EA=10:1) to give intermediate DK as a liquid (51 g, yield 64%). 1H NMR (CDCl3, 400 MHz): δ 7.22˜7.29 (m, 3H), 7.08 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 4.10 (t, J=4.8 Hz, 2H), 3.86 (t, J=4.8 Hz, 2H), 3.38-3.32 (m, 1H), 0.62-0.66 (m, 2H), 0.49-0.52(m, 2H).

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, and dried over Na2SO4
  6. concentrationThe residue was concentrated
  7. custompurified by flash column chromatography on silica gel (eluent PE:EA=10:1)

출처 및 근거

ORD 기록
ord-a26a10f0c88e41828db8bdc7112f7a53
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106021B2

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