Dichloromethane → HCID 86673524, compound

HRID 1424554Notes

Reaction equation

HRID 1424554 reaction equation
[N+:1]([C:4]1[C:5]([C:16]#[C:17][Si](C)(C)C)=[C:6]([C:10]#[C:11][Si](C)(C)C)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F-:22].[Cs+].[F:24][C:25]1[N:30]=[C:29]([F:31])[C:28]([F:32])=[C:27](F)[C:26]=1[F:34].ClCCl>CN(C=O)C.[Cl-].[Na+].O>[N+:1]([C:4]1[C:5]([C:16]#[C:17][C:27]2[C:28]([F:32])=[C:29]([F:31])[N:30]=[C:25]([F:24])[C:26]=2[F:34])=[C:6]([C:10]#[C:11][C:27]2[C:26]([F:22])=[C:25]([F:24])[N:30]=[C:29]([F:31])[C:28]=2[F:32])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 69690PentafluoropyridineHCID 11565908HCID 11565908, compound

Product 1

HCID 86673524HCID 86673524, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of ((3-nitro-1,2-phenylene)bis(ethyne-2,1-diyl))bis(trimethylsilane) (2.89 g, 9.16 mmol) in DMF (20 mL) was added into 20 mL of CsF(4.17 g, 27.5 mmol) solution in DMF. Into the mixture, pentafluoropyridine (3.87 g, 22.9 mmol) was added slowly at 0° C. The reaction mixture was stirred for 20 hrs, and brine (50 mL) and dichloromethane (100 mL) were added. Organic phase was separated and washed with water (50 mL×3). Solvent was evaporated by rotary evaporation and the residue was chromatographed (CH2Cl2:Hexane=1:4 to 1:3) to provide the desired product in 42% yield: 1H-NMR (300 MHz, CDCl3) δ 8.28 (dd, J=8.1 Hz, J=1.2 Hz, 1H), 8.02 (dd, J=7.8 Hz, J=1.2 Hz, 1H), 7.71 (dd, J=8.4 Hz, J=8.4 Hz, 1H)

Workup

  1. customOrganic phase was separated
  2. washwashed with water (50 mL×3)
  3. customSolvent was evaporated by rotary evaporation
  4. customthe residue was chromatographed (CH2Cl2:Hexane=1:4 to 1:3)

Sources & evidence

ORD record
ord-c5d8f2a5497842c3bf9bb3cf3bbf6835
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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