Sodium hydride → [3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid tert-butyl ester

HRID 270460Notes

Reaction equation

HRID 270460 reaction equation
[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][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].OS([O-])(=O)=O.[K+]>C1COCC1>[C:25]([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)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 516920Potassium bisulfateHCID 135847952HCID 135847952, compound

Product 1

HCID 69289771[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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) t-butyl 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).

Workup

  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

Sources & evidence

ORD record
ord-0d37225541ff486ea95f20bd19317180
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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