Bromoacetate → HCID 69289771, 화합물

HRID 347231

반응식

HRID 347231 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:6][CH:5]=1.Br[CH2:21][C:22]([O-:24])=[O:23].OS([O-])(=O)=O.[K+]>C1COCC1>[C:7]([O:24][C:22](=[O:23])[CH2:21][O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([C:7]3[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=3)=[N:11][S:12][C:13]=2[CH:18]=1)([CH3:10])([CH3:8])[CH3:6]

참가 물질

6

반응물 4

HCID 6226BromoacetateHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 135847952HCID 135847952, 화합물

생성물 1

HCID 69289771HCID 69289771, 화합물수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 0.74 g (16.9 mmol) NaH (55% in mineral oil) in 40 ml THF was added a solution of 4 g (13.1 mmol) 3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-ol in 20 ml THF at RT. The solution was stirred at RT for 1 h, 2.1 ml (14.3 mmol) tbutyl bromoacetate was added. The solution was stirred at RT over night, 1M KHSO4 was added carefully and the layers separated. The inorganic one was extracted with EtOAc, the combined organic phases were washed with water and brine and dried over Na2SO4. Column chromatography on silica gel with EtOAc:hexane 1:4 yielded 4.95 g (90%) [3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid tert-butyl ester as colorless oil, MS: 420 (MH+,1Br).

후처리

  1. stirringThe solution was stirred at RT over night
  2. customthe layers separated
  3. extractionThe inorganic one was extracted with EtOAc
  4. washthe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-f82690dc2fd04ad8bc1ee22e7c5fbe5a
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173043B2

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