1-Bromo-4-nitrobenzene → (E)-3-Cyclohexyl-2-(4-nitro-phenyl)-prop-2-en-1-ol

HRID 2103641ノート

反応式

HRID 2103641 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.[CH:11]1(/[CH:17]=[C:18](\B2OC(C)(C)C(C)(C)O2)/[CH2:19][OH:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[F-].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C1(P([Pd-4](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)C=CC=CC=1>[CH:11]1(/[CH:17]=[C:18](\[C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:19][OH:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

7

反応物 3

HCID 114661-Bromo-4-nitrobenzeneHCID 25953Cesium fluorideHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

生成物 1

HCID 67084428(E)-3-Cyclohexyl-2-(4-nitro-phenyl)-prop-2-en-1-ol収率 68.2%

試薬・触媒・溶媒 3

HCID 178420553HCID 178420553、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

Add tetrakis(triphenylphosphino)palladium(0) (0.60 g, 0.52 mmol) to a solution of 1-bromo-4-nitro-benzene (0.76 g, 3.76 mmol) and (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.13 g, 4.24 mmol) in dioxane (20 mL). Add cesium fluoride (1.75 g, 12 mmol) and stir the reaction mixture for 12 h at 80° C. Allow the reaction mixture to cool to r.t. Dilute the reaction mixture with ethyl acetate and wash with water. Separate the layers. Dry the organic phase over sodium sulfate, filter and concentrate. Purify the residue via silica gel chromatography, eluting with a gradient from 95:5 to 7:3 hexanes:ethyl acetate to obtain the title compound (0.67 g). 1H-NMR (CDCl3) δ=1.05-1.72 (m, 10 H), 1.89-2.04 (m, 1H), 4.28-4.36 (m, 2H), 5.61-5.69 (m, 1H), 7.34-7.43 (m, 2H), 8.18-8.26 (m, 2H).

後処理

  1. washwash with water
  2. customSeparate the layers
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue via silica gel chromatography
  7. washeluting with a gradient from 95:5 to 7:3 hexanes

出典と根拠

ORDレコード
ord-1af79803a3204b4fb639cc0c29c6849b
出典データセット
uspto-grants-2009_08
特許番号
US07576108B2

反応ノート

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