Potassium Carbonate → 5-Bromo-2-{[(2-fluorophenyl)methyl]oxy}benzonitrile

HRID 2264819노트

반응식

HRID 2264819 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[F:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 27570145-Bromo-2-hydroxybenzonitrile

생성물 1

HCID 226837045-Bromo-2-{[(2-fluorophenyl)methyl]oxy}benzonitrile수율 92%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of 5-bromo-2-hydroxybenzonitrile (3.31 g, 16.71 mmol), synthesized as described in J. Org. Chem. 1997, 13, 4504-4506, 2-fluorobenzylbromide (commercially available, 2.02 ml, 3.16 g, 16.71 mmol) and potassium carbonate (3.46 g, 25.06 mmol) was stirred overnight at room temperature. Then diethylether was added and the solution was washed with water, 1M NaOH and brine. The organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound (4.74 g, 92%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.0 (M, 1H), 7.9 (m, 1H), 7.6 (m, 1H), 7.5-7.3 (m, 2H), 7.2 (m, 2H), 5.3 (s, 2H).

후처리

  1. washthe solution was washed with water, 1M NaOH and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-b8f4965a1ce64d77afc5e627f1378c18
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855218B2

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