Hydrochloric Acid → Methyl 2-(bromomethyl)-5-nitrobenzoate

HRID 862435Notes

Reaction equation

HRID 862435 reaction equation
[N+](C1C=C(C(C)=CC=1)C(O)=O)([O-])=O.[N+:14]([C:17]1[CH:18]=[C:19]([C:24]([CH3:27])=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21])([O-:16])=[O:15].Cl.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C.CO>[Br:29][CH2:27][C:24]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 5196832-Methyl-5-nitrobenzoic acidHCID 4377758Methyl 2-methyl-5-nitrobenzoate2×

Product 1

HCID 14552709Methyl 2-(bromomethyl)-5-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

3-Nitro-6-methylbenzoic acid (2-1) (Aldrich) was converted into methyl 3-nitro-6-methylbenzoate (2-2) using the standard procedure of MeOH and HCl gas. To a mixture of methyl 3-nitro-6-methylbenzoate (2-2) (2.0 g, 10.3 mmol) and N-bromosuccinimide (1.64 g, 9.23 mmol) in CHCl3 was added AIBN (20 mg) and this was then photolysed at reflux for 4 hours. The reaction was cooled, filtered and the filtrate evaporated to dryness. Chromatography of the residue (silica, hexane/EtOAc 92:8) afforded 2-3 as a solid (1.56 g). Rf (silica; hexane/EtOAc 10:1)=0.25. ##STR57## N-t-Butoxycarbonylglycyl-3(R)-methyl-β-alanine benzyl ester (2-4)

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-3cbd14826dfa447886569ad687758d04
Source dataset
uspto-grants-1998_02
Patent number
US05719144

Reaction notes

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