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

HRID 1666378
ノート
印刷プレビュー

反応式

HRID 1666378 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2373f4e82567404c9b8598c0a1d00e49
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044052B2

反応ノート

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