Methanol → 2-Naphthalenecarboxylic acid, 1-bromo-, methyl ester

HRID 1889276Notes

Reaction equation

HRID 1889276 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:13][C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[Br:1])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 886651-Bromo-2-naphthoic acid

Product 1

HCID 109453332-Naphthalenecarboxylic acid, 1-bromo-, methyl ester

Procedure

To 2.00 g 1-bromo-naphthalene-2-carboxylic acid in 20 ml of dry methanol 5 ml of sulfuric acid were added. After 5 h at reflux, the reaction was poured onto ice-water, and the precipitated product was collected by filtration and washed until neutral. After recrystallization from heptane 1.90 g 1-bromo-naphthalene-2-carboxylic acid methyl ester were obtained.

Workup

  1. temperatureAfter 5 h at reflux
  2. additionthe reaction was poured onto ice-water
  3. filtrationthe precipitated product was collected by filtration
  4. washwashed until neutral
  5. customAfter recrystallization from heptane 1.90 g 1-bromo-naphthalene-2-carboxylic acid methyl ester
  6. customwere obtained

Sources & evidence

ORD record
ord-f30b336fbf94477aa8c73299c448f5b0
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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