Water → HCID 66726628, compound

HRID 1020794Notes

Reaction equation

HRID 1020794 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([F:16])[CH:10]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OCC)(=O)C.O>C1COCC1>[Br:17][C:12]1[C:13]([CH3:15])=[CH:14][C:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[CH:10][C:11]=1[F:16].[Br:17][C:14]1[C:13]([CH3:15])=[CH:12][C:11]([F:16])=[CH:10][C:9]=1[O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 66726507Benzene, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-fluoro-5-methyl-

Product 2

HCID 66726453HCID 66726453, compoundHCID 66726628HCID 66726628, compoundYield 184.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(3-fluoro-5-methylphenoxy)dimethylsilane (17.0 g, 70.8 mmol) in THF (300 mL) as added N-bromosuccinimide (18.9 g, 106 mmol) at room temperature, and the mixture was stirred for 1 h. The mixture was poured into ethyl acetate and water. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (98:2 hexane/ethyl acetate) to give a mixture (ca. 4:1) of (4-bromo-3-fluoro-5-methylphenoxy)(tert-butyl)dimethylsilane and (2-bromo-5-fluoro-3-methylphenoxy)(tert-butyl)dimethylsilane (20.9 g).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (98:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a216a5505e654a98832c234bdee7f802
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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