N-bromobutanimide → Ethyl 3-bromo-2-hydroxy-6-methyl-5-((methylsulfonyl)oxy)benzoate

HRID 577555Notes

Reaction equation

HRID 577555 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[C:5]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(#N)C>[Br:19][C:3]1[C:2]([OH:1])=[C:7]([C:6]([CH3:13])=[C:5]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86723781HCID 86723781, compound

Product 1

HCID 86723782Ethyl 3-bromo-2-hydroxy-6-methyl-5-((methylsulfonyl)oxy)benzoateYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 6-hydroxy-2-methyl-3-((methylsulfonyl)oxy)benzoate (116c, 1.3 g, 4.8 mmol) in acetonitrile (63 mL) was added N-bromosuccinimide (1.1 g, 6.2 mmol). The reaction was stirred at room temperature for 20 hours. The reaction mixture was concentrated under vacuum then diluted with water (30 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over magnesium sulfate, concentrated under vacuum, and purified by column chromatography (30% EtOAc/Heptane) to give ethyl 3-bromo-2-hydroxy-6-methyl-5-((methylsulfonyl)oxy)benzoate (116d, 1.3 g, 79% yield) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthen diluted with water (30 mL)
  3. extractionextracted with dichloromethane (2×50 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. custompurified by column chromatography (30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-412e725d5850438f96a6c40863d7a67e
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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