Bromoacetate → HCID 69289771, compound

HRID 347231Notes

Reaction equation

HRID 347231 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 69289771HCID 69289771, compoundYield 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-f82690dc2fd04ad8bc1ee22e7c5fbe5a
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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