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

HRID 734308ノート

反応式

HRID 734308 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 877924-Bromothiophene-2-carbaldehyde

生成物 1

HCID 27744523-(4-Bromothiophen-2-yl)acrylic acid収率 115.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-06b3702fa2b440b5bead22d1420ff004
出典データセット
uspto-grants-2009_09
特許番号
US07592352B2

反応ノート

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