二氯甲烷 → HCID 118452647，化合物

HRID 1773241

反应方程式

HRID 1773241 反应方程式
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].[CH3:16][C:17]1(C)[C:21](C)(C)OB(C(C)=C)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]([O:11][C:12]([F:15])([F:14])[F:13])=[C:2]([C:17]([CH3:21])=[CH2:16])[CH:7]=1)([O-:10])=[O:9]

参与物

9

反应物 4

HCID 6344二氯甲烷HCID 10340Carbonic acid sodium salt (1:2)HCID 10997426异丙烯基硼酸频哪醇酯HCID 247216412-溴-4-硝基-1-(三氟甲氧基)苯

产物 1

HCID 118452647HCID 118452647，化合物收率 93.6%

试剂、催化剂与溶剂 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次HCID 8071乙二醇二甲醚溶剂HCID 8857乙酸乙酯溶剂

实验过程

2-bromo-4-nitro-1-(trifluoromethoxy)benzene (0.56 g, 1.97 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.50 g, 2.96 mmol), PdCl2(dppf).CH2Cl2 adduct (0.16 g, 0.20 mmol), and Na2CO3 (0.63 g, 5.92 mmol) were combined in a 20 mL microwave vial and DME (15.78 mL) and Water (3.94 mL) were added. The mixture was stirred at RT for 6 s and then heated to 120° C. in the microwave for 30 min. The crude mixture was diluted with EtOAc and Water. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was diluted with DCM and silica gel was added. The mixture was concentrated under reduced pressure to dry-load material for purification. The crude was purified via silica gel FCC, 100% Heptane-100% EtOAc to give 4-nitro-2-(prop-1-en-2-yl)-1-(trifluoromethoxy)benzene (456 mg). 1H NMR (400 MHz, DMSO-d6) δ 2.08-2.13 (m, 3H), 5.21 (p, J=1.0 Hz, 1H), 5.43 (p, J=1.5 Hz, 1H), 7.68 (dq, J=9.0, 1.6 Hz, 1H), 8.21 (d, J=2.9 Hz, 1H), 8.28 (dd, J=9.0, 2.9 Hz, 1H).

后处理

  1. temperatureheated to 120° C. in the microwave for 30 min
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude was diluted with DCM and silica gel
  7. additionwas added
  8. concentrationThe mixture was concentrated under reduced pressure
  9. customto dry-load material
  10. customfor purification
  11. customThe crude was purified via silica gel FCC, 100% Heptane-100% EtOAc

来源与证据

ORD记录
ord-51b6b1bb5fa94c2ca2e94bc982a643d7
来源数据集
uspto-grants-2016_02
专利号
US09255093B2

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