Potassium Carbonate → 5-(4-Methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester

HRID 424792

반응식

HRID 424792 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH3:12])[CH:4]=1.[CH3:13][O:14][C:15]([C:17]1[S:18][C:19](Br)=[C:20]([CH3:22])[CH:21]=1)=[O:16].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.[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>[CH3:13][O:14][C:15]([C:17]1[S:18][C:19]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:12])=[C:20]([CH3:22])[CH:21]=1)=[O:16]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 2795489Methyl 5-bromo-4-methylthiophene-2-carboxylate

생성물 1

HCID 667042235-(4-Methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester수율 39.1%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a mixture of 4-methoxy-2-methylphenylboronic acid (912 mg, 6 mmol), 5-bromo-4-methyl-thiophene-2-carboxylic acid methyl ester (1.1 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in toluene (30 mL) and water (5 mL) is bubbled N2 for 15 minutes followed by addition of tetrakis(triphenylphosphine) palladium (289 mg, 0.25 mmol). The reaction mixture is stirred at 80° C. under N2 overnight. The reaction mixture is filtered through a diatomaceous earth pad eluting with EtOAc. The combined filtrate is concentrated and the residue is purified by column chromatography on silica gel eluting with 0-15% EtOAc in hexanes to give 5-(4-methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester (540 mg, 39%). 1H NMR (CDCl3): δ 7.63 (s, 1H), 7.15 (d, 1H, J=8.4 Hz), 6.82 (d, 1H, J=2.8 Hz), 6.78 (dd, 1H, J=2.8, J=8.4 Hz), 4.79 (bs, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 2.17 (s, 3H), 2.02 (s, 3H).

후처리

  1. customis bubbled N2 for 15 minutes
  2. filtrationThe reaction mixture is filtered through a diatomaceous earth pad
  3. washeluting with EtOAc
  4. concentrationThe combined filtrate is concentrated
  5. customthe residue is purified by column chromatography on silica gel eluting with 0-15% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-2f2beeb32f9641ea98cfa1f7a9d1f493
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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