Methanol → Methyl (4-bromo-2-fluorophenyl)acetate

HRID 1050010Notes

Reaction equation

HRID 1050010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:12])[CH:3]=1.OS(O)(=O)=O.[CH3:18]O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:18])=[O:10])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 140537922-(4-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 53429406Methyl (4-bromo-2-fluorophenyl)acetateYield 94%

Procedure

To a solution of 2-(4-bromo-2-fluorophenyl)acetic acid (260 g, 1.13 mol) in MeOH (2 L) was added H2SO4 (30 mL) at rt. The solution was heated to reflux overnight. Then the solvent was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. Another batch was repeated using the same procedure. Then the two batches were combined to provide methyl 2-(4-bromo-2-fluorophenyl)acetate (520 g, 94%). TLC (PE/EA=10:1, Rf=0.7). 1H NMR (400 MHz, CDCl3) δ 7.25-7.20 (m, 2H), 7.14 (t, J=8.0 Hz, 1H), 3.70 (s, 3H), 3.62 (s, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. concentrationThen the solvent was concentrated
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3227e726472b4027910fe81b072de792
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

Loading…