Methanol → HCID 75487957, compound

HRID 1779020Notes

Reaction equation

HRID 1779020 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].OS(O)(=O)=O.[CH3:21]O>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH3:21])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2778431[2-Bromo-4-(trifluoromethyl)phenyl]acetic acid

Product 1

HCID 75487957HCID 75487957, compound

Procedure

A solution of 2-bromo-4-trifluoromethylphenylacetic acid (2.00 g, 7.07 mmol) and concentrated aqueous H2SO4 (1 mL) in MeOH (30 mL) was heated at reflux for 16 hours. The volatiles were removed under reduced pressure then the residue taken up in EtOAc. The resulting solution was washed with 10% NaHCO3, dried (MgSO4) and evaporated under reduced pressure to give the title compound A57 as a clear liquid (2.07 g, 98%); 1H NMR (400 MHz, CDCl3) δ 7.83 (d, J=1.1 Hz, 1H), 7.53 (dd, J=8.0, 1.1 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 3.84 (s, 2H), 3.72 (s, 3H). LCMS-A: rt 6.236 min; m/z 297/299 [M+H]+.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe volatiles were removed under reduced pressure
  3. washThe resulting solution was washed with 10% NaHCO3
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2903861883374e7ab40cb98c074a4430
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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