Water → Methyl 2-(2-bromo-1-benzothiophen-3-yl)-2-(tert-butoxy)acetate

HRID 590964Notes

Reaction equation

HRID 590964 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([CH:18]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]([O:21][CH3:22])=[O:20])=[CH:10]1.O>C(#N)C>[Br:1][C:10]1[S:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]=1[CH:18]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 70813710Methyl 2-(1-benzothiophen-3-yl)-2-(tert-butoxy)acetate

Product 1

HCID 70813729Methyl 2-(2-bromo-1-benzothiophen-3-yl)-2-(tert-butoxy)acetateYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (67 mg, 0.37 mmol) was added at room temperature to a stirred solution of methyl 2-(1-benzothiophen-3-yl)-2-(tert-butoxy)acetate (4b) (70 mg, 0.25 mmol) in acetonitrile (2 mL) under a nitrogen atmosphere. After 20 hours, water (10 mL) was added and the reaction mixture was extracted with dichloromethane (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (4c) as a pale oil (40 mg, 0.11 mmol, 45%).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (2×10 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-44f5cbeafb6b4fdc9a1c743a8fb6ef00
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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