Dimethylformamide → 2,5-Dithien-2-ylterephthalic acid chloride

HRID 1473807Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=C(C(O)=O)[C:12]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][C:7]=1[C:8](O)=[O:9].[C:23](Cl)(=O)[C:24]([Cl:26])=[O:25].CN(C=O)C.C(Cl)[Cl:35]>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[C:23]([C:24]([Cl:26])=[O:25])[C:12]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][C:7]=1[C:8]([Cl:35])=[O:9]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 65578Oxalyl chloride

HCID 584350232,5-Dithien-2-ylterephthalic acid

Product 1

HCID 584350102,5-Dithien-2-ylterephthalic acid chlorideYield 97%

Conditions

Temperature: 23 °C

Procedure

To a solution of 2,5-dithien-2-ylterephthalic acid (4.06 g, 12.29 mmol) and oxalyl chloride (3.12 g, 24.58 mmol) in DCM (100 cm3) is added DMF (1 cm3) at 0° C. After 10 minutes, this mixture is allowed to warm to 23° C. and stirred overnight. The solvent is removed under reduced pressure to give the crude product as a yellow oil (4.38 g, 97%). 1H NMR (300 MHz, CDCl3): δ(ppm) 7.90 (s, 2H, Ar—H), 7.51 (dd, J=4.9 and 1.4 Hz, 2H, Ar—H), 7.13-7.20 (m, 4H, Ar—H). This product is used for next step without further purification.

Workup

customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-386e5c5dffe94991a5bc7ed146677ba2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09017577B2

Reaction notes

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