Bis(2-bromoethyl) ether → 4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

HRID 57529

반응식

HRID 57529 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[O:3]1.Br[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br.CCN(C(C)C)C(C)C>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([N:15]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[CH:13][CH:14]=2)[O:5]1

참가 물질

5

반응물 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 41926634-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (164 mg, 0.75 mmol), 1-bromo-2-(2-bromoethoxy)ethane (418 mg, 1.8 mmol), and DIPEA (0.64 mL, 3.6 mmol) in THF (2 mL) was stirred at reflux overnight. The mixture was concentrated, diluted with water, and extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin-layer chromatography to give the title compound. MS (m/z): 290 (M+H)+.

후처리

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin-layer chromatography

출처 및 근거

ORD 기록
ord-cc1fb27aad36408cadc3dd063474605a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

연결된 노트

불러오는 중…