Sodium Carbonate → 4-(3'-Acetyl-biphenyl-4-ylmethoxy)-2-hydroxy-benzoic acid

HRID 18437

반응식

HRID 18437 반응식
Br[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([OH:17])[CH:9]=2)=[CH:4][CH:3]=1.[C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:22])[CH3:21].C([O-])([O-])=O.[Na+].[Na+]>COCOC.O>[C:20]([C:23]1[CH:28]=[C:27]([C:2]2[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]3[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([OH:17])[CH:9]=3)=[CH:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH3:21]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 100418454-(4-Bromo-benzyloxy)-2-hydroxy-benzoic acid

생성물 1

HCID 100900294-(3'-Acetyl-biphenyl-4-ylmethoxy)-2-hydroxy-benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8020Dimethoxymethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-(4-bromo-benzyloxy)-2-hydroxy-benzoic acid (196.3 mg; 0.6075 mmol), 3-acetylbenzene boronic acid (99.7 mg; 0.6080 mmol) and Na2CO3 (−4 eq.) was dissolved in dimethoxymethane (4 mL) and H2O (2 mL). The solution was flushed with argon, Cl2Pd(PPh3)2 (˜2.5 mol %) was added and the mixture stirred under an atmosphere of argon at 100° C. for 16 hours. The resulting black solution was filtered (Gelman Acrodisc GHP, Ø25 mm) and slowly added to a cold 1 M HCl (aq.; 15 mL) solution. The precipitate was filtered off and thoroughly washed with water. Drying in vacuo yielded 195 mg (88%) of a greyish, solid compound with satisfactorily purity. Mp. 215-220° C. (decomposes); MS (ESI−): 361 (MH−)

후처리

  1. customThe solution was flushed with argon, Cl2Pd(PPh3)2 (˜2.5 mol %)
  2. additionwas added
  3. filtrationThe resulting black solution was filtered (Gelman Acrodisc GHP, Ø25 mm)
  4. additionslowly added to a cold 1 M HCl (aq.; 15 mL) solution
  5. filtrationThe precipitate was filtered off
  6. washthoroughly washed with water
  7. customDrying in vacuo
  8. customyielded 195 mg (88%) of a greyish, solid compound with satisfactorily purity

출처 및 근거

ORD 기록
ord-55fd6e29a2c646b2a517a85c518633b8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741352B2

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