Water → 3-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid

HRID 1725882Notes

Reaction equation

HRID 1725882 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:19].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[Br:19][C:15]1[C:14]([CH3:18])=[C:10]([C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 222451232-((tert-Butoxycarbonyl)amino)-6-methylbenzoic acidHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 688664473-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 104A (10 g, 40 mmol) and tetrabutylammonium tribromide (19.2 g, 40 mmol) in DMF (250 mL) was treated slowly with water (250 mL). The resulting suspension was stirred for 18 hours and partitioned between water (1.2 L) and ethyl acetate (500 mL). The organic layer was washed with water (2×1 L), dried (Na2SO4), filtered, and concentrated. The residue was dissolved in dichloromethane (900 mL), washed with water (5×1 L) and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (11.7 g). MS (ESI(−)) m/e 328, 330 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.60 (br s, 1H), 9.68 (s, 1H), 7.63 (d, 1H), 7.39 (d, 1H), 2.37 (s, 3H), 1.44 (s, 9H).

Workup

  1. custompartitioned between water (1.2 L) and ethyl acetate (500 mL)
  2. washThe organic layer was washed with water (2×1 L)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in dichloromethane (900 mL)
  7. washwashed with water (5×1 L) and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-184c9bdfbf784ffe92c977493bde5054
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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