Hydrochloric Acid → HCID 58764106, compound

HRID 859734Notes

Reaction equation

HRID 859734 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH3:11].[CH3:13][Mg]Br.Cl.C([O:19][CH2:20][CH3:21])C>>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:20]([OH:19])([CH3:21])[CH3:13])=[C:5]([CH3:11])[CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 58764106HCID 58764106, compoundYield 72%

Procedure

To 4-bromo-2-methyl-benzoic acid methyl ester (3.7 g, 15.9 mmol) in diethyl ether (10 mL) at 0° C. under N2 was added 3N methylmagnesium bromide in diethyl ether (21 mL, 63 mmol). The mixture was stirred 16 h at room temperature. The mixture was poured into 1N hydrochloric acid (aq, 10 mL) and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (MgSO4), filtered, and concentrated in vacuo to a crude colorless oil. Flash chromatography (SiO2, 5% ethyl acetate/hexane) gave the title compound as a colorless oil (2.6 g, 72%). 1H NMR (300 MHz, CDCl3): δ ppm 1.63 (s, 6 H) 2.56 (s, 3 H) 7.26–7.34 (m, 3 H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude colorless oil

Sources & evidence

ORD record
ord-1c914cffafa840129660b82581c87f11
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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