Hydrochloric Acid → Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

HRID 425295

반응식

HRID 425295 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1F.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[Br:16]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 79178Dimethyl 2-fluoroterephthalate

생성물 1

HCID 57839250Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-fluoro-terephthalic acid dimethyl ester 2j (10 g, 47.1 mmol), 2-bromophenol 1j (6.0 mL, 51.8 mmol) and potassium carbonate (7.16 g, 51.8 mmol) in N,N-dimethylformamide (100 mL) was heated at 100° C. for 36 h. The mixture was allowed to cool to rt, then poured into cold dilute hydrochloric acid (0.5 N, 350 mL). The product was extracted into EtOAc, washed with water (4×) and brine (1×) and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel using dichloromethane as the eluant. The crude product was isolated (10.5 g) and used without further purification in the subsequent reaction. MS: m/z 365 (MH+).

후처리

  1. temperatureto cool to rt
  2. extractionThe product was extracted into EtOAc
  3. washwashed with water (4×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-9aa268fa9af64837b4fe9febf42eaf06
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106207B2

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