Potassium Carbonate → Methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylate

HRID 219815노트

반응식

HRID 219815 반응식
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1Br)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[C:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=[CH:14][C:15]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH3:26])(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 22574808Methyl 3-(acetoxymethyl)-4-bromobenzoate

생성물 1

HCID 67400282Methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylate수율 100.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of methyl 3-[(acetyloxy)methyl]-4-bromobenzoate (4.7 g; 16.4 mmol; 1 eq.), o-tolylboronic acid (2.45 g; 18 mmol; 1.1 eq.), potassium carbonate (11.3 g; 82 mmol; 5 eq.) and Pd(PPh3)4 (1.89 g; 1.64 mmol; 0.1 eq.) in toluene (23.5 mL) and water (23.5 mL) was refluxed for 2 hours. After cooling to RT, the reaction mixture was filtered through a pad of Celite® which was further washed with toluene (50 mL). The filtrate was concentrated in vacuo, the residue taken up in EtOAc (250 mL) and washed with sat. aq. NaHCO3 (100 mL), water (100 mL) and brine (100 mL), dried over magnesium sulphate and concentrated in vacuo to afford the title compound (4.9 g, quantitative) as a brown oil. HPLC (Method A) Rt 5.23 min (Purity 62.3%).

후처리

  1. temperaturewas refluxed for 2 hours
  2. filtrationthe reaction mixture was filtered through a pad of Celite® which
  3. washwas further washed with toluene (50 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. washwashed with sat. aq. NaHCO3 (100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-06a5c4ca5c36451197af89b23f789600
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

반응 노트

불러오는 중…