Phenol → Phenyl 2-cyanobenzoate

HRID 1361802

反応式

HRID 1361802 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])#[N:2].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6])#[N:2]

参加物

7

反応物 4

HCID 996PhenolHCID 8471TriethylamineHCID 1380612-Cyanobenzoic acidHCID 2724699PyBOP

生成物 1

HCID 23144259Phenyl 2-cyanobenzoate収率 90.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-Cyanobenzoic acid (1.00 g, 6.80 mmol), phenol (576 mg, 6.12 mmol) and PyBOP (3.90 g, 7.48 mmol) were dissolved in DMF (12 mL), and triethylamine (2.10 mL, 15.0 mmol) was added thereto, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:2) to afford phenyl 2-cyanobenzoate (1.24 g, 82%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:2)

出典と根拠

ORDレコード
ord-7d297e5eddc842c4b71e8cb051382c4a
出典データセット
uspto-grants-2011_02
特許番号
US07880013B2

関連ノート

読み込み中…