Potassium Carbonate → 4-(1,3-Thiazol-2-yl)benzaldehyde

HRID 8972

반응식

HRID 8972 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:12]1[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 5910734-Formylphenylboronic Acid

생성물 1

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehyde수율 15%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-bromothiazole (0.26 g, 1.6 mmol) and 4-formylphenylboronic acid (0.48 g, 3.2 mmol) in toluene (16 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.09 g, 0.08 mmol) and K2CO3 (0.33 g, 2.4 mmol) and the solution stirred at reflux for 16 h. The reaction was cooled to room temperature, diluted with water (50 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine (30 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (2% MeOH/CH2Cl2) to give 4-(2-thiazolyl)-benzaldehyde (45 mg, 15%). 1H NMR (CDCl3) δ 7.45 (d, 1H, J=3.0 Hz), 7.90 (d, 1H, J=3.0 Hz), 7.97 (d, 2H, J=7.8 Hz), 8.15 (d, 2H, J=7.2 Hz), 10.07 (s, 1H (CHO)).

후처리

  1. temperatureat reflux for 16 h
  2. customThe organic layer was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-7a2f34a04f1b42dcbdbae8ab9077148c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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