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

HRID 2264819ノート

反応式

HRID 2264819 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b8f4965a1ce64d77afc5e627f1378c18
出典データセット
uspto-grants-2010_12
特許番号
US07855218B2

反応ノート

読み込み中…