Nitrogen → Methyl 4-(bromomethyl)benzoate

HRID 2081186Notes

Reaction equation

HRID 2081186 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:12][Si](C=[N+]=[N-])(C)C.N#N.C(OCC)(=O)C>CO.C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:12])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 225994-(Bromomethyl)benzoic acidHCID 167693Trimethylsilyldiazomethane2×

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1.0 eq of 4-(bromomethyl)benzoic acid in 20 ml of methanol and 50 ml of toluene; was added dropwise 2.05 eq of trimethylsilyldiazomethane while stirring at room temperature. The reaction was titrated until a persistant pale yellow color existed from the addition of excess trimethylsilyldiazomethane. Let stir at room temperature for 1 hr to insure the complete evolution of N2. Thin layer chromatography in 1:1 hexame:ethyl acetate indicated the disappearance of starting material and the appearance of desired ester with an Rf of 0.7.

Workup

  1. stirringLet stir at room temperature for 1 hr

Sources & evidence

ORD record
ord-73f3775e80524b249c778e89ffc1d528
Source dataset
uspto-grants-1993_02
Patent number
US05183810

Reaction notes

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