Methanol → Dimethyl 4-bromoisophthalate

HRID 2414220

반응식

HRID 2414220 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]CCCCC.[CH3:25][OH:26]>>[CH3:25][O:26][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([C:11]([O:13][CH3:19])=[O:12])[CH:4]=1

참가 물질

5

반응물 4

HCID 887Methanol2회HCID 1118Sulfuric AcidHCID 8058HexaneHCID 813614-Bromo-1,3-benzenedicarboxylic acid

생성물 1

HCID 2824912Dimethyl 4-bromoisophthalate수율 90%

실험 절차

To a solution of 4-bromoisophthalic acid 201 (10 g, 40.8 mmol) in methanol (150 mL) was added concentrated sulfuric acid (3.5 mL). The solution mixture was heated at reflux temperature for 24 hours. After the reaction was complete, the methanol solvent was removed under reduced pressure. The residue was made basic with saturated sodium bicarbonate (NaHCO3). The solution was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate (Na2SO4). Removal of solvent gave oil, which solidified at ambient temperature. The solid was titurated twice with 20 mL of methanol and hexane (1:3) to give 8 g (90%) of 4-bromoisophthalic acid dimethyl ester 202: 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 3H), 3.93 (s, 3H), 7.74 (d, J=8 Hz, 1H), 7.95 (dd, J=2 Hz, J=8 Hz, 1H), 8.43 (d, J=2 Hz, 1H).

후처리

  1. temperatureThe solution mixture was heated
  2. temperatureat reflux temperature for 24 hours
  3. customthe methanol solvent was removed under reduced pressure
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulfate (Na2SO4)
  7. customRemoval of solvent
  8. customgave oil, which
  9. customsolidified at ambient temperature

출처 및 근거

ORD 기록
ord-b866ac2847c048d28510d69a8450aa6d
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06811979B2

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