Diethyl Ether → 4-Bromo-2-fluoro-alpha,alpha-dimethylbenzenemethanol
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5](C(OC)=O)=[C:4]([F:12])[CH:3]=1.[CH3:13][Mg+].[Br-].CC[O:18][CH2:19][CH3:20]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:19]([OH:18])([CH3:20])[CH3:13])=[C:4]([F:12])[CH:3]=1Participants
4
Conditions
- Temperature
- 25 °C
Procedure
A solution of methyl 4-bromo-2-fluorobenzoate (8.0 g, 34.3 mmol) in anhydrous Et2O (85 mL) was treated with MeMgBr (3.0 M in THF, 30 mL). The resulting solution was stirred at 25° C. for 3 hours before it was quenched by the addition of H2O (10 mL). The mixture was extracted with EtOAc (50 mL) three times and the combined organic extracts were washed with aqueous NH4Cl, brine, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (0–25% EtOAc in hexanes) to give the desired product (7.2 g, 91% yield).
Workup
- customwas quenched by the addition of H2O (10 mL)
- extractionThe mixture was extracted with EtOAc (50 mL) three times
- washthe combined organic extracts were washed with aqueous NH4Cl, brine
- dry with materialdried over Na2SO4
- customThe solvent was removed in vacuo
- customthe residue was purified by flash column chromatography (0–25% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-9de288be93f6447394a83d2862cee279
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148226B2
Reaction notes
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