Tetrahydrofuran → 3-(4-Bromo-3-methyl-phenyl)-pentan-3-ol

HRID 546870Notes

Reaction equation

HRID 546870 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([CH3:15])[CH:9]=1.[Cl-].[NH4+].O1CC[CH2:21][CH2:20]1>>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([OH:16])([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:9][C:10]=1[CH3:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 574330783-(4-Bromo-3-methyl-phenyl)-pentan-3-olYield 97%

Conditions

Temperature
0 °C

Procedure

Ethylmagnesium bromide (3 M solution in diethyl ether, 73 mL, 218.3 mmol) was added to a solution of 4-bromo-3-methylbenzoic acid methyl ester (20 g, 87.31 mmol) in tetrahydrofuran (120 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for one hour. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50) to give the target compound as a colorless oil (21.86 g, 97%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-d4884b94ae524f6d83822b1e6dc6add5
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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