Succinic anhydride → 4-(4-Bromo-2-methylphenyl)-4-oxobutanoic acid

HRID 735637Notes

Reaction equation

HRID 735637 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.C([Mg]Br)(C)C.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 27246015-Bromo-2-iodotolueneHCID 178418365HCID 178418365, compound

Product 1

HCID 247270004-(4-Bromo-2-methylphenyl)-4-oxobutanoic acidYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-1-iodo-2-methylbenzene (148 mg, 0.5 mmol) in THF (10 mL) at −25° C. was added isopropylmagnesium bromide (0.5 mL, 0.5 mmol) and stirred 3 h. Succinic anhydride (55 mg, 0.55 mmol) was added and the reaction was stirred 18 h. The mixture was quenched with water (10 mL) and washed with 1N NaOH (10 mL), 1N HCl (10 mL), brine (10 mL) and dried (MgSO4). The organic layer was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtOAc/Hexane) to afford 55A (42 mg, 31%) as a crystalline solid. 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (t, 3 H) 2.42 (q, 2 H) 2.73 (t, 2 H) 4.10 (t, 2 H) 6.82 (d, 1 H) 7.02 (d, 1 H) 7.09 (t, 2 H) 7.15 (t, 1 H) 7.36 (d, 1 H) 7.58-7.63 (m, 1 H).

Workup

  1. stirringthe reaction was stirred 18 h
  2. customThe mixture was quenched with water (10 mL)
  3. washwashed with 1N NaOH (10 mL), 1N HCl (10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue purified by flash chromatography (0-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-7a8fab20a3e84cb185831c372aee819c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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