Hydrochloric Acid → Methyl 2-Bromo-5-chlorobenzoate

HRID 1058273Notes

Reaction equation

HRID 1058273 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 890272-Bromo-5-chlorobenzoic acid

Product 1

HCID 280500Methyl 2-Bromo-5-chlorobenzoateYield 92%

Procedure

Into a stirred solution of 2-bromo-5-chlorobenzoic acid (11 g, 46.7 mmol, HPLC RT=2.99 min) in methanol (250 mL) at 0° C. was bubbled HCl gas. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated in vacuo to give an orange oil, which was purified by flash chromatography using hexanes as eluant to give methyl 2-bromo-5-chlorobenzoate as a colorless oil (10.7 g, 92% yield). TLC Rf=0.6 (5% EtOAc-hexanes); HPLC RT=3.48 min, method A; 1H NMR (CDCl3, 400MHz) 7.78 ppm (d, 1H, J=2.6 Hz); 7.59 ppm (d, 1H, J=12.81 Hz); 7.30 ppm (dd, 1H, J=8.6, 2.5 Hz); 3.94 ppm (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give an orange oil, which
  3. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-2a6f5ea38a234f2e821c5b90c40a10b7
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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