Water → 4-(4-Trifluoromethylphenyl)thiophene-2-carbaldehyde

HRID 9639

反応式

HRID 9639 の反応式
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[CH:13][C:14]([C:6]2[CH:2]=[C:3]([CH:7]=[O:8])[S:4][CH:5]=2)=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

生成物 1

HCID 117369544-(4-Trifluoromethylphenyl)thiophene-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

To a solution of 3-bromothiophene-2-carboxaldehyde (2.0 g) and 3-trifluoromethylbenzene boronic acid (2.19 g) in ethylene glycol dimethyl ether (100 ml) was added sodium carbonate (2.9 g), tetrakis(triphenylphosphine) palladium (0) (0.12 g) and water (50 ml). The mixture was heated to 90° C. under nitrogen. After 18 hours the reaction was allowed to cool and was concentrated. The residue was partitioned between water and ethyl acetate; the organic solution was taken and was washed with brine and then dried (MgSO4) and concentrated. The crude material was purified by SPE (Si); the product eluted with neat chloroform to furnish the title compound as a yellow solid.

後処理

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customThe residue was partitioned between water and ethyl acetate
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by SPE (Si)
  8. washthe product eluted with neat chloroform

出典と根拠

ORDレコード
ord-ffa3f6e62ec945dc861cc1427e46b8f0
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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