2-Butyn-1-ol → Methyl 4-bromo-2-fluoro-6-hydroxybenzoate

HRID 452457Notes

Reaction equation

HRID 452457 reaction equation
[Br:1][C:2]1[CH:11]=[C:10](F)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:13])[CH:3]=1.C([OH:18])C#CC.CC(C)([O-])C.[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]([OH:18])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 129912-Butyn-1-olHCID 23665647Potassium tert-butoxideHCID 26343953Methyl 4-bromo-2,6-difluorobenzoate

Product 1

HCID 66886502Methyl 4-bromo-2-fluoro-6-hydroxybenzoateYield 38.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 4-bromo-2,6-difluorobenzoate (0.5 g, 2.0 mmol), 2-butyn-1-ol (0.16 ml, 2.1 mmol), potassium tertbutoxide (0.47 g, 4.2 mmol) in dry DMSO (5 ml) was heated in a microwave oven at 125° C. for 2.5 min. The reaction mixture was cooled to ambient temperature and quenched with water. The mixture was acidified with aqueous HCl (1 M) and extracted with EtOAc, dried (Na2SO4), filtered and evaporated to dryness to afford an oil. Purification by flash column chromatography (isooctane/EtOAc 10:1) gave the title compound (0.19 g, 35%). MS m/z (rel. intensity, 70 eV) 250 (M+, 43), 248 (M+, 44), 218 (96), 216 (bp), 190 (44),188 (45).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto afford an oil
  7. customPurification by flash column chromatography (isooctane/EtOAc 10:1)

Sources & evidence

ORD record
ord-371354475ae144e1bdc9cf4d246f89ae
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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