Cesium carbonate → Diethyl(4-nitrophenyl)phosphonate

HRID 472666

반응식

HRID 472666 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[P:17]([O-:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:19]([O:18][P:17]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:20]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 114661-Bromo-4-nitrobenzeneHCID 3780918Diethylphosphite

생성물 1

HCID 284865Diethyl(4-nitrophenyl)phosphonate

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

A mixture of 1-bromo-4-nitrobenzene (400 mg, 2.00 mmol), tetrakis(triphenylphosphine)palladium(0) (120 mg, 0.20 mmol) and cesium carbonate (734 mg, 2.2 mmol) in a 30 mL microwave vial was purged and backfilled with nitrogen. Tetrahydrofuran (20 mL) was added followed by diethyl phosphite (0.360 mL, 2.8 mmol). The mixture was vortexed, then microwaved for 45 minutes at 120° C. Reaction was repeated three times to achieve total scale then the combined reaction mixtures were purified via chromatography (120 g silica gel 5%->75% ethyl acetate in hexane). (4-Nitro-phenyl)-phosphonic acid diethyl ester isolated as a light yellow oil (969 mg, 47%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.35 (d, J=8.0 Hz, 2H), 7.16 (s, 1H), 5.93 (s, 2H), 3.40 (s, 4H), 2.36 (s, 4H), 2.20 (s, 3H), 8.05-7.95 (m, 2H), 4.09 (m, 4H), 1.25 (t, J=13.8, 7.4 Hz, 6H).

후처리

  1. customwas purged
  2. additionTetrahydrofuran (20 mL) was added
  3. custommicrowaved for 45 minutes at 120° C
  4. customReaction
  5. customthe combined reaction mixtures
  6. customwere purified via chromatography (120 g silica gel 5%->75% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-2493498a82fd449393526b3bf9ea033c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

연결된 노트

불러오는 중…