Cesium carbonate → Diethyl(4-nitrophenyl)phosphonate

HRID 472666

反応式

HRID 472666 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 284865Diethyl(4-nitrophenyl)phosphonate

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2493498a82fd449393526b3bf9ea033c
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

関連ノート

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