Hydrochloric Acid → 3-(4-Bromo-2,5-difluorophenyl)acrylic acid

HRID 533942

Reaction equation

HRID 533942 reaction equation
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1(C)[O:18]C(=O)CC(=O)[O:14]1.Cl>C(N(CC)CC)C>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[CH:12][C:13]([OH:18])=[O:14])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 224890814-Bromo-2,5-difluorobenzaldehyde

Product 1

HCID 867151273-(4-Bromo-2,5-difluorophenyl)acrylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 4-bromo-2,5-difluorobenzaldehyde (15.0 g) in triethylamine formiate (80 mL) at room temperature was added 2,2-dimethyl-1,3-dioxane-4,6-dione (9.77 g). After being stirred for 1 h, the mixture was heated at 95° C. with stirring for 15 hours. After cooling down, ice water was added. The mixture was adjusted to pH ˜1 with HCl (6 M) and then extracted with ethyl acetate (200 mL×3). The organic phase was washed with brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography eluting with DCM/petroleum ether (7:1) to give the subtitle compound as a white solid. MS ESI+: m/z=263 [M+H]+.

Workup

  1. stirringwith stirring for 15 hours
  2. temperatureAfter cooling down
  3. extractionextracted with ethyl acetate (200 mL×3)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with DCM/petroleum ether (7:1)

Sources & evidence

ORD record
ord-1bc5e5f3c76f442fbf793ad34471c903
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Linked notes

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