2-Bromo-4-nitroanisole → 2-Bromo-4-nitrophenol

HRID 458086

반응식

HRID 458086 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11]C>CN(C=O)C.CCOC(C)=O.Cl>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11]

참가 물질

5

반응물 1

HCID 788702-Bromo-4-nitroanisole

생성물 1

HCID 221092-Bromo-4-nitrophenol수율 52.3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

2-Bromo4-nitroanisole (20 g, 0.086 mol) was dissolved in DMF (414 mL) at rt under N2. Sodium ethylthiolate (17.4 g, 0.207 mol) was added and the reaction mixture was warmed to 115° C. for 2 h. The reaction was cooled to rt and diluted with EtOAc (200 mL) and 1 M HCl (aq., 200 mL). The phases were separated, and the desired product was extracted into 1 M NaOH (aq, 150 mL×3). The basic aqueous extracts were combined and acidified using conc. HCl. The desired product was extracted from the acidic aqueous solution using EtOAc (250 mL×2). The combined organic layers were washed with brine and dried over sodium sulfate. The volatiles were removed in vacuo to afford a light brown semi-solid (9.8 g, 52% yield). 1H NMR (DMSO-d6) δ 8.33 (m, 1H); 8.09 (m, 1H); 7.07 (d, 1H).

후처리

  1. temperatureThe reaction was cooled to rt
  2. customThe phases were separated
  3. extractionthe desired product was extracted into 1 M NaOH (aq, 150 mL×3)
  4. extractionThe desired product was extracted from the acidic aqueous solution
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-8c964f0ad2554b1996530ab96f95cdac
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189734B2

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