Allyl bromide → Methyl 3-[allyl(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate

HRID 507007Notes

Reaction equation

HRID 507007 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:12]([O:14][CH3:15])=[O:13])=[O:7].[CH2:26](Br)[CH:27]=[CH2:28]>C1COCC1>[CH2:28]([N:8]([C:6](=[O:7])[C:5]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:4]=1[Br:3])[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:27]=[CH2:26]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 2673200Methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate

Product 1

HCID 67018574Methyl 3-[allyl(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaH (680 mg [60% dispersion in oil]) in THF (250 ml) at 0° C. was added methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate (5.36 g) portionwise. The reaction was stirred for 30 minutes at room temperature when allyl bromide (1.6 ml) was added dropwise and the solution was stirred for a further 20 hours at room temperature. The reaction mixture was quenched with water and then concentrated. The residue was dissolved in ethyl acetate and washed with water (×2), brine, dried (magnesium sulfate) and concentrated. The residue was purified by column chromatography on a silica column eluting using a gradient of iso-hexane to 50% ethyl acetate/iso-hexane to yield methyl 3-[allyl(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate as a colourless oil (4.88 g); Mass Spectrum: M+H+ 417.

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water (×2), brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on a silica column
  9. washeluting

Sources & evidence

ORD record
ord-5e296b344d4a4837baebf597892a2bb8
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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