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Diethyl [chloro(4-chlorophenyl)methyl]phosphonate → 2-[5-(4-Chlorophenylethynyl)thien-2-ylethynyl]benzothiophene

HRID 1460994
Notes
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Reaction equation

HRID 1460994 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]#[C:9][C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[CH:14]=2)=[CH:5][CH:4]=1)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26](P(=O)(OCC)OCC)Cl)=[CH:22][CH:21]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:1][C:3]2[S:7][C:6]([C:8]#[C:9][C:10]3[S:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[CH:14]=3)=[CH:5][CH:4]=2)=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12881548Diethyl [chloro(4-chlorophenyl)methyl]phosphonateHCID 199814132-(5-Formylthien-2-ylethynyl)benzothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 199814142-[5-(4-Chlorophenylethynyl)thien-2-ylethynyl]benzothiopheneYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 0.75 gram (0.0028 mole) of 2-(5-formylthien-2-ylethynyl)benzothiophene and 0.83 gram (0.0028 mole) of diethyl (4-chlorophenyl)chloromethylphosphonate in 10 ml of dimethylformamide was cooled to 0° C., and 0.94 gram (0.0084 mole) of potassium tertbutoxide was added. Upon completion of addition, the reaction mixture was stirred at 0° C. for 30 minutes and then was allowed to warm to ambient temperature where it was stirred for 18 hours. After this time the reaction mixture was subjected to column chromatography on silica gel. Elution was accomplished using hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.20 gram of 2-[5-(4-chlorophenylethynyl)thien-2-ylethynyl]benzothiophene; m.p. 189°-191° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureto warm to ambient temperature where it
  3. stirringwas stirred for 18 hours
  4. washElution
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6ff885b78e642bc83fdfeade4a57314
Source dataset
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05073564

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes