Dichloromethane → HCID 118452647, 화합물

HRID 1773241

반응식

HRID 1773241 반응식
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]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 247216412-Bromo-4-nitro(trifluoromethoxy)benzene

생성물 1

HCID 118452647HCID 118452647, 화합물수율 93.6%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-51b6b1bb5fa94c2ca2e94bc982a643d7
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255093B2

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