Diethyl Ether → 2-(3-Bromophenyl)propan-2-ol

HRID 1991530Notes

Reaction equation

HRID 1991530 reaction equation
[CH3:1][Mg]Br.COC(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1.CC[O:17][CH2:18][CH3:19]>C1COCC1>[Br:13][C:9]1[CH:8]=[C:7]([C:18]([OH:17])([CH3:19])[CH3:1])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12070Methyl 3-bromobenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 150723832-(3-Bromophenyl)propan-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6° C. is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0° C. and quenched by dropwise addition of aqueous 10% HCl. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHCO3 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15% ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93%) of 2-(3-bromophenyl)-2-propanol 27 as a pale yellow oil: 1H NMR (CDCl3) δ 7.65 (t, J=2 Hz, 1H), 7.39 (m, 2H), 7.20 (t, J=8 Hz, 1H), 1.78 (br s, 1H), 1.57 (s, 6H).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of aqueous 10% HCl
  3. extractionThe acidified mixture is extracted twice with ethyl acetate
  4. washthe combined organic phases are washed with 1 N NaHCO3 and with brine
  5. dry with materialThe solution is dried over Na2SO4
  6. concentrationconcentrated
  7. customchromatographed over silica gel
  8. washeluting with 15% ethyl acetate in heptane

Sources & evidence

ORD record
ord-a54ed395d0d0487899c5fb1792d20772
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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