Methyl 4-bromobenzoate → HCID 21034016, compound

HRID 1512684Notes

Reaction equation

HRID 1512684 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].C([Li])CCC.CO[C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1>C1COCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[O:5][N:4]=[C:2]([CH3:3])[CH:1]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 12081Methyl 4-bromobenzoateHCID 67180Acetone, oximeHCID 178418339Butyllithium

Product 1

HCID 21034016HCID 21034016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetone oxime (4.85 g, 66.4 mmol) was dissolved in THF (100 mL) and cooled to 0° C. n-Butyllithium (1.6M in hexanes, 81 mL, 129.6 mmol) was added and the reaction was stirred at room temperature for 1 hour. 4-Bromo-benzoic acid methyl ester (9.4 g, 43.7 mmol) in THF (30 mL) and the reaction stirred for 24 hours. The mixture was submitted to standard aqueous workup then dried over MgSO4 and evaporated. The residue was taken up in EtOH and HCl (4N in dioxane, 1 mL) was added. The reaction was heated to 60° C. and monitored by analytical TLC. When completed, the reaction mixture was concentrated to dryness to afford the title compound, which was used directly in the next step.

Workup

  1. additionwas added
  2. dry with materialthen dried over MgSO4
  3. customevaporated
  4. additionHCl (4N in dioxane, 1 mL) was added
  5. temperatureThe reaction was heated to 60° C.
  6. concentrationthe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-08bebb688c2948ceab2f551827ee623f
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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