Toluene → HCID 67304258, compound

HRID 2362482Notes

Reaction equation

HRID 2362482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:20]1(C)C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:12])[C:9]([O:11][CH3:20])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 673039292-(3-Bromophenyl)-2-(tert-butoxycarbonyl)propanoic acid

Product 1

HCID 67304258HCID 67304258, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-bromophenyl)-2-(tert-butoxycarbonyl) propanoic acid (11.3 g, 32.8 mmol) in MeOH (35 mL) was added toluene (175 mL) followed by TMSCHN2 (2M in hexane, 44 mL, 98 mmol, 3 eq). The mixture was stirred at RT for 16 h. Solvents were evaporated and the residue was chromatographed on silica by eluting with EtOAc/hexanes to give 11.8 g (100%) of methyl 2-(3-bromophenyl)-2-(tert-butoxycarbonyl)propanoate as a yellow oil. 1H NMR (CDCl3) 7.59 (t, J=1.8 Hz, 1H), 7.36-7.44 (m, 2H), 7.21 (t, J=8.0 Hz, 1H), 5.92 (s, 1H), 3.70 (s, 3H), 1.97 (s, 3H), 1.36 (br s, 9H).

Workup

  1. customSolvents were evaporated
  2. customthe residue was chromatographed on silica
  3. washby eluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-a2ca3de6f91c450293cd3878f8462e6f
Source dataset
uspto-grants-2014_04
Patent number
US08691831B2

Reaction notes

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