4-Bromoaniline → HCID 6420877, compound

HRID 1826211Notes

Reaction equation

HRID 1826211 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16]>O1CCCC1.O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15](=[O:16])[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 78074-BromoanilineHCID 62365Isobutyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 6420877HCID 6420877, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromoaniline (10.0 g, 58.1 mmol) in tetrahydrofuran (230 mL) was treated with sodium bicarbonate (9.77 g, 116.2 mmol) and water (100 mL) followed by isobutyl chloroformate (8.3 mL, 63.9 mmol), and the mixture was stirred at ambient temperature for 2 hrs. The mixture was then diluted with water (100 mL) and EtOAc (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Recrystallization of the resulting solid from EtOAc/hexanes provided the title compound, mp 95-96° C.; MS (ESI−) for C11H14NO2Br m/z 270 (M−H)−.

Workup

  1. customthe layers were separated
  2. washthe organic phase was washed with water (50 mL) and saline (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization of the resulting solid from EtOAc/hexanes

Sources & evidence

ORD record
ord-5129c026b2ab44ba96ac7e6770b7d9ea
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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