Tetrahydrofuran → 3-(3-Bromophenyl)pentan-3-ol

HRID 546828Notes

Reaction equation

HRID 546828 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1.[Cl-].[NH4+].O1CC[CH2:20][CH2:19]1>>[Br:14][C:10]1[CH:9]=[C:8]([C:7]([OH:15])([CH2:1][CH3:2])[CH2:19][CH3:20])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 12070Methyl 3-bromobenzoateHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 574434823-(3-Bromophenyl)pentan-3-ol

Procedure

Ethylmagnesium bromide (3 mol/l solution in diethyl ether, 34.1 mL, 102.3 mmol) was added to a solution of 3-bromobenzoic acid methyl ester (10 g, 46.51 mmol) in tetrahydrofuran (100 mL) in a nitrogen atmosphere at −78° C. The mixture was stirred at the same temperature for one hour and then heated to room temperature. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure to give crude 3-(3-bromo-phenyl)-pentan-3-ol.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b17793dd7c874776b4e04a10ec4d17f3
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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