N-bromobutanimide → 7-Bromo-9-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-on

HRID 1803210Notes

Reaction equation

HRID 1803210 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:25][C:20]3([O:24][CH2:23][CH2:22][O:21]3)[CH2:19][CH:18]=[C:17]2[O:26][Si](C)(C)C)=[CH:12][CH:11]=1>C1COCC1.O.CCOC(C)=O>[Br:1][CH:18]1[C:17](=[O:26])[CH:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH2:25][C:20]2([O:24][CH2:23][CH2:22][O:21]2)[CH2:19]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66858541(9-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-8-yloxy)trimethylsilane

Product 1

HCID 581101137-Bromo-9-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-onYield 253%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Step AAC (2): Followed a method described by A. de Meijer et. al Chem. Eur. J. 2007, 13, 3739. N-bromosuccinimide (52 mg, 0.29 mmol) was added to a solution of (9-(4-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-8-yloxy)trimethylsilane (89 mg, 276 mmol) in THF/water (1:1, 1.4 mL). The resulting mixture was allowed to stir for 2 hr. The crude reaction was diluted with EtOAc and washed with water. The organic layer was concentrated in vacuo to afford 7-bromo-9-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-on (230 mg, 253%) yield). The crude product was used for subsequent chemistry without purification or characterization.

Workup

  1. customThe crude reaction
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-8f08471f7412444ead89459a4021daba
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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