Hydrochloric Acid → 3-(4-Bromothiophen-2-yl)acrylic acid

HRID 734308Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.Cl>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])[S:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 4-bromo-thiophene-2-carbaldehyde (10 g, 0.052 mol), malonic acid (6.5 g, 0.063 mol) and piperidine (0.5 ml) in pyridine (40 ml) was stirred for 14 hours at 100° C., which was cooled down to room temperature and poured into water, and resultant mixture was acidified with concentrated HCl. The generated precipitate was collected by filtration, which was suspended with EtOH (50 ml) and water (100 ml). The precipitate was collected by filtration and dried under the reduced pressure to give 3-(4-bromo-thiophen-2-yl)-acrylic acid (14 g). 1H NMR (400 MHz, DMSO-d6) ppm 7.79 (s, 1H), 7.67 (d, J=15.9 Hz, 1H), 7.56 (s, 1H), 6.26 (d, J=15.9 Hz, 1H).

Workup

temperaturewhich was cooled down to room temperature
filtrationThe generated precipitate was collected by filtration, which
filtrationThe precipitate was collected by filtration
customdried under the reduced pressure

Sources & evidence

ORD record: ord-06b3702fa2b440b5bead22d1420ff004
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592352B2

Reaction notes

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