Methyl 3-bromobenzoate → 3-(5-Bromo-2-pyridyl)-3-pentanol

HRID 1454405Notes

Reaction equation

HRID 1454405 reaction equation
CO[C:3](=O)[C:4]1C=CC=C(Br)C=1.[C:12](OC1C=CC(Br)=CC=1C)(=O)[CH3:13].C([C:26]1[C:27]([C:33]([OH:35])=O)=[N:28][CH:29]=[C:30]([Br:32])[CH:31]=1)C.C([Mg]Br)C>C(Cl)Cl>[Br:32][C:30]1[CH:31]=[CH:26][C:27]([C:33]([OH:35])([CH2:12][CH3:13])[CH2:3][CH3:4])=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 12070Methyl 3-bromobenzoateHCID 600267744-Bromo-2-methylphenyl acetateHCID 67144082Ethyl-5-bromo-2-carboxypyridine2×HCID 178418443HCID 178418443, compound

Product 1

HCID 116873863-(5-Bromo-2-pyridyl)-3-pentanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compounds were prepared using methyl-3-bromobenzoate, methyl-4-bromophenyl acetate, ethyl-5-bromo-2-carboxypyridine or ethyl-5-bromo-2-carboxypyridine and ethyl magnesium bromide with methylene chloride as solvent, respectively, but otherwise followed the procedure detailed for Preparation 36.

Workup

  1. customdetailed for Preparation 36

Sources & evidence

ORD record
ord-af4c73c20ef94e7181eed01fd20518e4
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

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