Bromine → Methy 4-amino-3-bromo-5-[(2-hydroxy-2-methylpropyl)amino]benzoate

HRID 592328Notes

Reaction equation

HRID 592328 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15].[Br:18]Br>C(Cl)Cl>[NH2:1][C:2]1[C:3]([NH:12][CH2:13][C:14]([OH:17])([CH3:15])[CH3:16])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[Br:18]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 66693495Methyl 4-amino-3-[(2-hydroxy-2-methylpropyl)amino]benzoate

Product 1

HCID 66693821Methy 4-amino-3-bromo-5-[(2-hydroxy-2-methylpropyl)amino]benzoateYield 26.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methy 4-amino-3-[(2-hydroxy-2-methylpropyl)amino]benzoate (1.5 g, 6.30 mmol) in DCM (12.59 mL) added bromine (0.324 mL, 6.30 mmol) drop-wise. The reaction was complete upon total addition of bromine. Reaction mixture was quenched with sodium sulfite and diluted with EtOAc. The aqueous layer was washed with EtOAc (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% TFA) gave the title compound (0.538 g): LC-MS [M]=317.2.

Workup

  1. customReaction mixture
  2. customwas quenched with sodium sulfite
  3. additiondiluted with EtOAc
  4. washThe aqueous layer was washed with EtOAc (3×)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-92b8a2c1fb1c4eebb1e173c7caa2d8c6
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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