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

HRID 9639

반응식

HRID 9639 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffa3f6e62ec945dc861cc1427e46b8f0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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