Benzoyl Peroxide → HCID 22266042, compound

HRID 489610Notes

Reaction equation

HRID 489610 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([CH3:16])[CH:15]=1)[O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([CH2:16][Br:17])[CH:15]=1)[O:5][Si:6]([C:9]([CH3:11])([CH3:12])[CH3:10])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 113356171-Bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-methylbenzene

Product 1

HCID 22266042HCID 22266042, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3-Bromo-5-methyl-phenoxy)-tert-butyldimethylsilane (3.32 mmol) [prepared according to the procedure of J. E. Baldwin et al, Tetrahedron, 1991, 47(29), 5603], N-bromosuccinimide (3.65 mmol), and benzoyl peroxide (0.332 mmol) were dissolved in dichloromethane (10 mL) and the reaction mixture irradiated for 4 hours. Diluted with dichloromethane and washed with water, dried over magnesium sulfate and concentrated to dryness. The crude material was purified by column chromatography on silica gel with 10% ethyl acetate/cyclohexane to give (3-bromo-5-bromomethyl-phenoxy)-tert -butyldimethylsilane as a colorless oil. This material was subjected to the conditions described in the first part of EXAMPLE 1A, but using (3-bromo-5-bromomethyl-phenoxy)-tert-butyldimethylsilane in place of 3-bromobenzylbromide, to give 3-bromo-N,N-(bis-tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxy)benzylamine as a colorless oil. MS (EI) 516 and 518 (M++H).

Workup

  1. customthe reaction mixture irradiated for 4 hours
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by column chromatography on silica gel with 10% ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-a98c70d5cdf0464b8dbf4d57c5a58d83
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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