Sodium Cyanide → 2-Bromo-5-cyanobenzoic acid

HRID 705717

반응식

HRID 705717 반응식
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]([Br:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].[C:16]([Cu])#[N:17].[C-]#N.[Na+]>O.Cl>[Br:15][C:9]1[CH:8]=[CH:7][C:6]([C:16]#[N:17])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

참가 물질

7

반응물 4

HCID 8929Sodium CyanideHCID 27696245-Amino-2-bromobenzoic acidHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 532567612-Bromo-5-cyanobenzoic acid

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매3회

반응 조건

온도
60 °C

실험 절차

A solution of NaNO2 (0.29 g, 4.2 mmol) in water (1.6 mL) was added dropwise to a solution of 5-amino-2-bromobenzoic acid (0.86 g, 4 mmol) in HCl 2N (6 mL) and water (6 mL) at 0° C. during 15 minutes. The reaction mixture was stirred for 20 minutes and then added dropwise to a solution of CuCN (0.7 g, 8 mmol) and NaCN (0.4 g, 8 mmol) in water (5 mL) at 60° C.; the mixture was heated at 60° C. for further 15 minutes. After cooling at room temperature HCl (2N) was added and the product was extracted twice with AcOEt; the combined organic layers were dried and evaporated to give the title compound as a brown solid. Yield (0.6 g, 67%).

후처리

  1. additionwas added
  2. extractionthe product was extracted twice with AcOEt
  3. customthe combined organic layers were dried
  4. customevaporated

출처 및 근거

ORD 기록
ord-79e483b1f5f04b3e80d5a1084a140852
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174977B2

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