Hydrochloric Acid → HCID 58764106, compound

HRID 2387124Notes

Reaction equation

HRID 2387124 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-7bba51be09bc49b3acbd6409c6abcf64
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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