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

HRID 1725899Notes

Reaction equation

HRID 1725899 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 (10 g, 30.3 mmol), potassium carbonate (6.3 g, 45.4 mmol), and DMF (300 mL) was treated with benzyl bromide (3.6 mL, 30.3 mmol), stirred for 5 hours, concentrated, and partitioned between water (1 L) and ethyl acetate (1 L). The organic layer was washed with water (2×1 L) and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 420, 422 (M+H)+, 437, 439 (M+NH4)+, 442, 444 (M+Na)+; (ESI(−)) m/e 418, 420 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.04 (s, 1H), 7.65 (d, 1H), 7.45 (m, 2H), 7.37 (m, 3H), 7.22 (d, 1H), 5.28 (s, 2H), 2.30 (s, 3H), 1.42 (s, 9H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between water (1 L) and ethyl acetate (1 L)
  3. washThe organic layer was washed with water (2×1 L) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59dd4f67165a4996a20127eaeb1f9ae3
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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