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Ethyl Acetate → Diethyl 3-(5-bromopyrimidin-2-yloxy)benzylphosphonate

HRID 1666378
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HRID 1666378 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]Cl)[CH:10]=2)=[N:6][CH:7]=1.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].C(OCC)(=O)C>CCCCCCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[CH2:15][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[N:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 668767225-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine

생성물 1

HCID 86623898Diethyl 3-(5-bromopyrimidin-2-yloxy)benzylphosphonate수율 83.5%

시약·촉매·용매 1

HCID 8900Heptane용매

반응 조건

온도
150 °C

실험 절차

5-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine (810 mg, 2.70 mmol) was treated with triethyl phosphite (1 mL, 2.2 mmol), and heated to 150° C. After 16 h, the reaction mixture was removed from the heat and ethyl acetate (about 3 mL) followed by heptane were added. As the reaction mixture cooled an oily precipitate formed. The mixture was made homogenous by addition of ethyl acetate. Heptane was added dropwise until a white solid precipitated. Additional heptane was added and the solid was filtered, washed with heptane and dried in vacuo to afford the title compound (0.737 g, 68% yield) as a white solid. MS (APCI) M+1=401; 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=6.92 Hz, 6H) 3.18 (d, J=21.64 Hz, 2H) 3.98-4.10 (m, 4H) 7.06-7.11 (m, 1H) 7.15 (q, J=2.01 Hz, 1H) 7.20-7.26 (m, 1H) 7.35-7.42 (m, 1H) 8.56 (s, 2H).

후처리

  1. customthe reaction mixture was removed from the
  2. temperatureheat
  3. additionwere added
  4. temperatureAs the reaction mixture cooled an oily precipitate
  5. customformed
  6. customprecipitated
  7. additionAdditional heptane was added
  8. filtrationthe solid was filtered
  9. washwashed with heptane
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-2373f4e82567404c9b8598c0a1d00e49
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

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