N-bromobutanimide → HCID 59857642, compound

HRID 2378077Notes

Reaction equation

HRID 2378077 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[CH:16][CH:15]=3)[CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:31]N1C(=O)CCC1=O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([O:20][Si:21]([CH:22]([CH3:23])[CH3:24])([CH:28]([CH3:29])[CH3:30])[CH:25]([CH3:27])[CH3:26])=[CH:18][CH:19]=3)[C:10]=2[Br:31])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59857603HCID 59857603, compound

Product 1

HCID 59857642HCID 59857642, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[3-(4-triisopropylsilanyloxy-phenyl)-isoxazol-5-yl]-cyclopropanecarboxylic acid ethyl ester (288 g) in 3 L DMF was cooled to 5° C. under an atmosphere of N2. The reaction solution was treated with N-bromosuccinimide (131.5 g) and allowed to slowly warm to room temperature over 20 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (2 L), cooled to −15° C., and quenched with 10% sodium metabisulfite solution (150 mL) with stirring. The organic layer was separated, washed with sat. NaHCO3 (250 mL) and brine (250 mL), dried over Na2SO4, filtered, and evaporated. The residue was purified by column chromatography (0 to 20% ethyl acetate in hexanes) to afford 1-[4-bromo-3-(4-triisopropylsilanyloxy-phenyl)-isoxazol-5-yl]-cyclopropanecarboxylic acid ethyl ester (285 g) as a light-brown thick liquid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (2 L)
  3. temperaturecooled to −15° C.
  4. customquenched with 10% sodium metabisulfite solution (150 mL)
  5. customThe organic layer was separated
  6. washwashed with sat. NaHCO3 (250 mL) and brine (250 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography (0 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3fb3208e78f949ea870cffa3f9c644f4
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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