2-Bromopyridine → 3-(Pyridin-2-yl)benzoic acid

HRID 415289노트

반응식

HRID 415289 반응식
B([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(O)O.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8]

참가 물질

7

반응물 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 27339573-Carboxyphenylboronic acid

생성물 1

HCID 51525923-(Pyridin-2-yl)benzoic acid수율 85%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100° C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85%. LC-MS (ESI) m/z: 200 (M+1)+.

후처리

  1. customThe mixture was degassed
  2. custompurged
  3. filtrationThen the hot suspension was filtered
  4. concentrationconcentrated to half of the original volume
  5. washwashed with dichloromethane
  6. filtrationfiltrated
  7. washwashed with water
  8. customThe residue was dried in vacuum

출처 및 근거

ORD 기록
ord-6069d7e6b68943bebcc42529e55df792
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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