Trimethylsilyldiazomethane → Methyl 4-[2-(2-bromo-5-methoxyphenyl)-1-methylethyl]benzoate

HRID 1880591Notes

Reaction equation

HRID 1880591 reaction equation
C[Si](C=[N+]=[N-])(C)C.[CH:8]1C=CC=CC=1.CO.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[CH2:25][CH:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)[CH3:27]>CC(O)=O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[CH2:25][CH:26]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:34][CH3:8])=[O:33])=[CH:35][CH:36]=1)[CH3:27]

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 21927730Benzene methanolHCID 674857104-[2-(2-Bromo-5-methoxyphenyl)-1-methylethyl]benzoic acid

Product 1

HCID 59756903Methyl 4-[2-(2-bromo-5-methoxyphenyl)-1-methylethyl]benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(Trimethylsilyl)diazomethane (2.0M hexanes, 4.8 mL) was added dropwise to a benzene/MeOH solution (7/3, 50 mL) containing the intermediate from Step A (2.8 g, 8.0 mmol). After 20 minutes AcOH was added dropwise to quench the excess reagent. The solution was concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.98 (d, J=8.2 Hz, 2H); 7.43 (d, J=8.2 Hz, 1H); 7.29 (d, J=8.2 Hz, 2H); 6.63 (dd, J=3.0, 8.7 Hz, 1H); 6.50 (d, J=3.0 Hz, 1H); 3.93 (s, 3H); 3.68 (s, 3H); 3.26-3.19 (m, 1H); 2.96 (d, J=7.0 Hz, 2H); 1.34 (d, J=6.9 Hz, 3H). LCMS1 4.14 min. (M-31)=331

Workup

  1. customto quench the excess reagent
  2. concentrationThe solution was concentrated
  3. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-715f8ba8b5f0443aa0c72f6cf5bb63f8
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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