N-Fluorobenzenesulfonimide → HCID 118537058, compound

HRID 923379Notes

Reaction equation

HRID 923379 reaction equation
[F:1][C:2]1[C:3]2[CH2:9][S:8][CH2:7][C:4]=2[S:5][CH:6]=1.C([Li])CCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:25])(=O)=O)=CC=1>O1CCCC1.O=O>[F:25][C:6]1[S:5][C:4]2[CH2:7][S:8][CH2:9][C:3]=2[C:2]=1[F:1]

Participants

6

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 86692647HCID 86692647, compoundHCID 178418339Butyllithium

Product 1

HCID 118537058HCID 118537058, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 8028TetrahydrofuranSolvent

Procedure

In an alternate embodiment, a method is described of producing a monomer wherein the method begins by dissolving 3-fluoro-4,6 dihydrothieno[3,4-b]thiophene in tetrahydrofuran in a non-oxygen atmosphere to create a solution. An initiator of n-butyllithium is then added to the solution to produce an initiated solution. This is followed by adding N-fluorobenzenesulfonimide to the initiated solution to produce 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene. 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene is then oxidized with meta-chloroperoxybenzoic acid to produce 2,3-difluorothieno[3,4-b]thiophene. 2,3-difluorothieno[3,4-b]thiophene is then bromoated with N-bromosuccinimide to produce 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene. The final step involves debrominating 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene and adding an aryl group to produce the monomer

Workup

  1. customof producing a monomer wherein the method
  2. customto produce an initiated solution

Sources & evidence

ORD record
ord-f0e64da5c7ec42acb31111251143759e
Source dataset
uspto-grants-2016_03
Patent number
US09278980B2

Reaction notes

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