Methanol → 3-Ethynyl-2,4-difluoro-1,5-dimethoxybenzene

HRID 1052309Notes

Reaction equation

HRID 1052309 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]#[C:14][Si](C)(C)C.CO.[F-].[Cs+]>O1CCCC1>[C:13]([C:3]1[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[F:12])#[CH:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 25953Cesium fluorideHCID 89963360[(2,6-Difluoro-3,5-dimethoxyphenyl)ethynyl](trimethyl)silane

Product 1

HCID 867191713-Ethynyl-2,4-difluoro-1,5-dimethoxybenzeneYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl](trimethyl)-silane (630 mg, 2.33 mmol) in tetrahydrofuran (2 mL)/methanol (2 mL), cesium fluoride (354 mg, 2.33 mmol) was added at room temperature. After 1 hour, the reaction was quenched with saturated aq. NH4Cl, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, concentrated to give the desired product (440 mg, 95%). 1H NMR (300 MHz, CDCl3): δ 6.62 (t, J=7.8 Hz, 1H), 3.89 (s, 7H) ppm.

Workup

  1. customthe reaction was quenched with saturated aq. NH4Cl
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f66a31523cb4a178920a52d0ee68cd3
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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