Cesium carbonate → 6-Fluoro-3',5'-dimethoxy-4-nitrobiphenyl-3-carbaldehyde

HRID 56463

반응식

HRID 56463 반응식
Br[C:2]1[C:3]([F:13])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:13][C:3]1[C:2]([C:18]2[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=2)=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 113796385-Bromo-4-fluoro-2-nitrobenzaldehyde

생성물 1

HCID 1180361436-Fluoro-3',5'-dimethoxy-4-nitrobiphenyl-3-carbaldehyde수율 73.7%

시약·촉매·용매 2

HCID 178479804HCID 178479804, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5-bromo-4-fluoro-2-nitrobenzaldehyde (10.0 g, 40.0 mmol), 3,5-dimethoxyphenylboronic acid (7.3 g, 40.0 mmol), bis(triphenylphosphino) palladium(II) chloride (1.4 g, 2.0 mmol) and cesium carbonate (32.6 g, 100.0 mmol) in dioxane/water (550 mL, v/v=10/1) was degassed with nitrogen for three times and heated at 90° C. for 3 hours. The mixture was cooled to room temperature, concentrated, diluted with ethyl acetate (1000 mL), and washed by water (500 mL) and brine (500 mL). The organic layer was dried, concentrated, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=8/1 to 5/1) to afford the title compound (9 g, 61%) as a yellow solid. MS (ES+) C15H12FNO5 requires: 305, found: 306 [M+H]+.

후처리

  1. customwas degassed with nitrogen for three times
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate (1000 mL)
  5. washwashed by water (500 mL) and brine (500 mL)
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=8/1 to 5/1)

출처 및 근거

ORD 기록
ord-da5102f3143b4fe5bc503d2f4daeb2f6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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