Cesium carbonate → 1-(Difluoromethoxy)-4-ethynylbenzene

HRID 271125

Reaction equation

HRID 271125 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.C(Cl)Cl.C(Cl)Cl>[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 68699091{[4-(Difluoromethoxy)phenyl]ethynyl}(trimethyl)silane

Product 1

HCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of {[4-(difluoromethoxy)phenyl]ethynyl}(trimethyl)silane (10.0 g, 41.7 mmol) in MeOH/CH2Cl2 (1/1) was treated with cesium carbonate (16.3 g, 50 mmol) at room temperature, stirred for 1.5 h, diluted with CH2Cl2 and filtered through a pad of silica gel. The filtrate was concentrated to dryness to give the title compound (6.8 g, 97%) as an oil. MS (+) EI: 168.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a871ee9c353348c1b6690fe365083eea
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Linked notes

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