4-Bromo-2-fluorobenzoic acid → 4-Bromo-2-ethylbenzoic acid

HRID 1503662Notes

Reaction equation

HRID 1503662 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](F)[CH:3]=1.[CH2:12]([Mg]Br)[CH3:13]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH2:12][CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 3026814-Bromo-2-fluorobenzoic acidHCID 178418443HCID 178418443, compound

Product 1

HCID 106570054-Bromo-2-ethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-bromo-2-fluorobenzoic acid (2.0 g, 9.17 mmol) in THF (16 mL), was added 1.0 M ethyl magnesium bromide in THF (32 mL, 32.0 mmol) dropwise at 0° C. and the resultant reaction mixture was stirred at RT for 18 h. The reaction mixture was quenched with 2 N HCl and extracted with ethyl acetate. The combined ethyl acetate layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude 4-bromo-2-ethylbenzoic acid as a colorless liquid that was used in the next step without purification (0.4 g): 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=8.4 Hz, 1H), 7.47 (m, 1H), 7.43 (m, 1H), 2.95 (q, J=4.0 Hz, 2H), 1.32 (t, J=4.0 Hz, 3H); ESIMS m/z 228.97 ([M+H]+).

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with 2 N HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fa964d873b54434b1734a7b3d8eb13a
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

Loading…