Water → HCID 59353046, compound

HRID 1914701Notes

Reaction equation

HRID 1914701 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F-].[Cs+].[CH2:15](B1OC(C)(C)C(C)(C)O1)[CH:16]=[CH2:17].O>C1COCC1.CCCCCC.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>[CH2:17]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH:16]=[CH2:15]

Participants

8

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 2926594-Iodo-3-nitroanisoleHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane

Product 1

HCID 59353046HCID 59353046, compoundYield 51.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (5 g, 18 mmol) in. THF (500 mL) are added cesium fluoride (11 g, 72 mmol) and Pd(PPh3)4(0.56 g, 48 mmol). The resulting mixture is stirred for 30 min at room temperature. A solution of allylboronic acid pinacol ester (5.6 mL, 33 mmol) in THF (15 mL) is added dropwise. The resulting mixture is refluxed for 24 h then diluted with hexane (100 mL) followed by water (100 mL). The product is extracted with hexane (2×100 mL). The combined organic layers are washed with water (150 mL) then brine (150 mL) and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by column chromatography using hexane as eluent affording 1.8 g (48%) of the title compound as a brown liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.93-7.91 (m, 1), 7.59-7.50 (m, 1H), 7.04-7.01 (m, 1H), 5.0-4.9 (m, 2H), 3.89-3.85 (m, 1H), 3.81 (s, 3H), 3.53-3.51 (m, 2H).

Workup

  1. temperatureThe resulting mixture is refluxed for 24 h
  2. extractionThe product is extracted with hexane (2×100 mL)
  3. washThe combined organic layers are washed with water (150 mL)
  4. dry with materialbrine (150 mL) and dried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-578340da5a3048c7bde14369d5eb930b
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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