Tetrahydrofuran → HCID 57443521, compound

HRID 547065Notes

Reaction equation

HRID 547065 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[Cl-].[NH4+].O1CC[CH2:20][CH2:19]1>>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([OH:15])([CH2:1][CH3:2])[CH2:19][CH3:20])=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 12081Methyl 4-bromobenzoateHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 57443521HCID 57443521, compoundYield 98%

Conditions

Temperature
0 °C

Procedure

Ethylmagnesium bromide (3 M solution in diethyl ether, 77.5 mL, 233 mmol) was added to a solution of 4-bromo-benzoic acid methyl ester (20 g, 93 mmol) in tetrahydrofuran (220 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for 30 minutes. 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 to give the target compound as a colorless oil (22.1 g, 98%).

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

Sources & evidence

ORD record
ord-a2f75b58981b4fb6a9ff8a451ea2a19d
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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