tert-Butyl methyl ether → Benzoic acid, 3-bromo-2-hydroxy-5-methoxy-, methyl ester

HRID 486289

반응식

HRID 486289 반응식
[Br:1]Br.[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[OH:14].COC(C)(C)C>CCCCCCC.O>[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([Br:1])[C:7]=1[OH:14]

참가 물질

6

반응물 3

HCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

생성물 1

HCID 11184546Benzoic acid, 3-bromo-2-hydroxy-5-methoxy-, methyl ester수율 82.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8900Heptane용매2회

실험 절차

In the course of from 30 to 45 minutes, at 20°, with stirring, 43.9 g of bromine are added dropwise to a solution of 45.9 g of 2-hydroxy-5-methoxy-benzoic acid methyl ester in 125 ml of heptane. The reaction mixture is then stirred for a further 3 to 4 hours, then diluted with 110 ml of water and stirred for a further one hour and then 295 ml of heptane and 46 ml of tert-butyl methyl ether are added thereto. The mixture is then heated to from 50° to 55° and the aqueous phase is separated off. The organic phase is extracted twice with 114 ml of water each time and cooled to -20°. The crystals which precipitate are filtered off and dried under a high vacuum. 3-Bromo-2-hydroxy-5-methoxy-benzoic acid methyl ester is thus obtained; yield 82.5% of the theoretical yield.

후처리

  1. stirringThe reaction mixture is then stirred for a further 3 to 4 hours
  2. stirringstirred for a further one hour
  3. temperatureThe mixture is then heated to from 50° to 55°
  4. customthe aqueous phase is separated off
  5. extractionThe organic phase is extracted twice with 114 ml of water each time
  6. temperaturecooled to -20°
  7. filtrationThe crystals which precipitate are filtered off
  8. customdried under a high vacuum

출처 및 근거

ORD 기록
ord-a893f363e49043b88b78e74c554c5397
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290939

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