Phenol → Phenyl 2-cyanobenzoate

HRID 1361802

반응식

HRID 1361802 반응식
[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]

참가 물질

7

반응물 4

HCID 996PhenolHCID 8471TriethylamineHCID 1380612-Cyanobenzoic acidHCID 2724699PyBOP

생성물 1

HCID 23144259Phenyl 2-cyanobenzoate수율 90.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7d297e5eddc842c4b71e8cb051382c4a
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880013B2

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