Benzyl Bromide → Benzyl 3-bromo-6-[(tert-butoxycarbonyl)amino]-2-methylbenzoate

HRID 1725887Notes

Reaction equation

HRID 1725887 reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:8]([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[CH:9][CH:10]=1)[C:5]([O:7][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 688664473-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid

Product 1

HCID 68864148Benzyl 3-bromo-6-[(tert-butoxycarbonyl)amino]-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 104B (5 g, 15.1 mmol), potassium carbonate (3.1 g, 22.7 mmol), and DMF (150 mL) was treated with benzyl bromide (1.8 mL, 15.1 mmol), stirred for 5 hours, and concentrated. The residue was partitioned between water (1 L) and dichloromethane (750 mL). The organic layer was washed with water and brine, dried (Na2SO4), filtered, concentrated, and purified by passing through a plug of silica gel (150 g) with 25% dichloromethane in hexane to provide the desired product. MS (ESI(−)) m/e 418, 420 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.05 (br s, 1H), 7.65 (d, 1H), 7.45 (m, 2H), 7.39 (m, 3H), 7.21 (d, 1H), 5.28 (s, 2H), 2.30 (s, 3H), 1.42 (s, 9H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water (1 L) and dichloromethane (750 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-b378246a5a314b9c92b73705edeaa816
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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