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

HRID 966357Notes

Reaction equation

HRID 966357 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])=[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]

Participants

6

Reactant 4

HCID 6226BromoacetateHCID 24758Sodium hydrideHCID 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) 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).

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-42fa74cf1dab4ba1a1990ab557f6bf34
Source dataset
uspto-grants-2005_10
Patent number
US06951879B2

Reaction notes

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