Diethyl Ether → 2-(5-Bromo-2-methoxyphenyl)propan-2-ol

HRID 2215382Notes

Reaction equation

HRID 2215382 reaction equation
[CH3:1][Mg]Br.COC(=O)[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=CC=1OC.[CH2:17]([O:19][CH2:20][CH3:21])C.[Cl-].[NH4+].[O:24]1[CH2:28][CH2:27]CC1>C(OCC)(=O)C>[Br:13][C:11]1[CH:12]=[CH:7][C:20]([O:19][CH3:17])=[C:21]([C:28]([CH3:27])([OH:24])[CH3:1])[CH:10]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 13297188Methyl 5-bromo-2-methoxybenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 219488782-(5-Bromo-2-methoxyphenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

62 ml of a 3 M methylmagnesium bromide solution in tetrahydrofuran is added in drops within one hour at 0° C. into 18.6 g of 5-bromo-2-methoxybenzoic acid methyl ester and 180 ml of diethyl ether. After 16 hours at room temperature and while being cooled with ice, it is mixed with saturated ammonium chloride solution and ethyl acetate. The ethyl acetate phase is washed with water, dried (Na2SO4) and concentrated by evaporation. After bulb tube distillation (boiling point: 140° C./0.04 hPa), 16.7 g of crystalline 1-(5-bromo-2-methoxyphenyl)-1-methylethanol is obtained. Flash point: 66–68° C.

Workup

  1. temperaturewhile being cooled with ice, it
  2. washThe ethyl acetate phase is washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. distillationAfter bulb tube distillation (boiling point: 140° C./0.04 hPa)

Sources & evidence

ORD record
ord-83c761ee75774f00afa57e474e5f50e1
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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