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Water → Dimethyl 2,5-di(thiophen-2-yl)terephthalate

HRID 1473805
Notes
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Reaction equation

HRID 1473805 reaction equation
Br[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9](Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br-].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[Zn+].O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:2]=1[C:19]1[S:18][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 874011,4-Dimethyl 2,5-dibromo-1,4-benzenedicarboxylateHCID 178419761HCID 178419761, compound

Product 1

HCID 1045411Dimethyl 2,5-di(thiophen-2-yl)terephthalateYield 87.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67 °C

Procedure

Dimethyl 2,5-dibromoterephthalate (6.09 g, 17.30 mmol) is dissolved in anhydrous THF (100 cm3), followed by the addition of 2-thienylzinc bromide (0.50 M in THF, 90 cm3, 45.0 mmol) and Pd(PPh3)4 (0.50 g, 0.43 mmol). The mixture is heated at 67° C. for 2 hours. After cooling, the reaction mixture is poured into water. The precipitate is collected by filtration and washed with water, methanol and diethyl ether then dried in vacuo, to yield the product as a pale yellow solid (5.41 g, 87%). 1H NMR (300 MHz, CDCl3): δ(ppm) 7.82 (s, 2H, Ar—H), 7.40 (dd, J=4.8 and 1.4 Hz, 2H, Ar—H), 7.07-7.12 (m, 4H, Ar—H), 3.78 (s, 6H, CH3); 13C NMR (75 MHz, CDCl3): δ(ppm) 168.1 (C═O), 140.3 (q), 133.6 (q), 133.4 (q), 131.9 (CH), 127.5 (CH), 127.0 (CH), 126.7 (CH), 52.6 (CH3); MS (m/e): 358 (M+, 100%), 327, 299, 240, 195.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water, methanol and diethyl ether
  4. customthen dried in vacuo

Sources & evidence

ORD record
ord-2dc0fb65827c49c58d7ffba3bbbd7409
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09017577B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes