Triethylamine → HCID 90314138、化合物

HRID 1505750ノート

反応式

HRID 1505750 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:14]1([C:17]#[CH:18])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C=O)C.C1(C)C=CC=CC=1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[C:17][CH:14]2[CH2:16][CH2:15]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 144749Ethyl 5-bromo-2-chlorobenzoate

生成物 1

HCID 90314138HCID 90314138、化合物収率 103.7%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of ethyl 5-bromo-2-chlorobenzoate (1.9 g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), dichloro bis(triphenylphosphine)palladium (1.01 g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100° C. under argon atmosphere for 8 hours, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated. By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86 g) was obtained as brown oil.

後処理

  1. customthe mixture was degassed
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. filtrationThe insoluble material was filtered off on celite
  5. washThe mother liquor was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customBy purification on column chromatography

出典と根拠

ORDレコード
ord-560e49dc0ade4467833eb5257c93f891
出典データセット
uspto-grants-2015_12
特許番号
US09216968B2

反応ノート

読み込み中…