Triethyl phosphite → Diethyl 3-(5-bromopyridin-2-yloxy)benzylphosphonate

HRID 1666371노트

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HRID 1666371 반응식
[Br:1][C:2]1[CH:3]=[CH: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.[CH2:17]([O:19][P:20]([O:24]CC)[O:21][CH2:22][CH3:23])[CH3:18]>CCCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[CH2:15][P:20](=[O:24])([O:21][CH2:22][CH3:23])[O:19][CH2:17][CH3:18])=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 31215Triethyl phosphiteHCID 198462395-Bromo-2-(3-(chloromethyl)phenoxy)pyridine

생성물 1

HCID 86623897Diethyl 3-(5-bromopyridin-2-yloxy)benzylphosphonate수율 81.3%

시약·촉매·용매 1

HCID 8900Heptane용매

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온도
150 °C

실험 절차

5-Bromo-2-(3-(chloromethyl)phenoxy)pyridine (3.08 g, 10.3 mmol) from Step 2 was treated neat with triethylphosphite (2.65 mL, 15.5 mmol) and heated to 150° C. After 5 h, the reaction mixture was removed from the heating bath and treated slowly with heptane until an oil precipitated out of solution. Ethyl acetate was added until mixture became homogenous. Heptane was slowly added again (at a cooler temperature) until a white precipitate formed. After the addition of more heptane and stirring for 15 min, the precipitate was filtered to afford a white solid (3.35 g, 81% yield). MS (APCI) M+1=400.0; 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=7.02 Hz, 6H) 3.17 (d, J=21.64 Hz, 2H) 3.98-4.08 (m, 4H) 6.84 (d, J=8.77 Hz, 1H) 7.00-7.05 (m, 1H) 7.08 (q, J=2.21 Hz, 1H) 7.15-7.20 (m, 1H) 7.35 (t, J=7.90 Hz, 1H) 7.77 (dd, J=8.58, 2.53 Hz, 1H) 8.21 (d, J=2.73 Hz, 1H).

후처리

  1. customthe reaction mixture was removed from the heating bath
  2. additiontreated slowly with heptane until an oil
  3. customprecipitated out of solution
  4. additionEthyl acetate was added until mixture
  5. additionHeptane was slowly added again (at a cooler temperature) until a white precipitate
  6. customformed
  7. filtrationthe precipitate was filtered

출처 및 근거

ORD 기록
ord-5f26e7f4a24d44ea9d26168db142fb63
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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