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

HRID 486289

反応式

HRID 486289 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8900Heptane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a893f363e49043b88b78e74c554c5397
出典データセット
uspto-grants-1994_03
特許番号
US05290939

関連ノート

読み込み中…