4-Bromoaniline → HCID 6420877, compound

HRID 1991254Notes

Reaction equation

HRID 1991254 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) is 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 is stirred at ambient temperature for 2 h. The mixture is then diluted with water (100 mL) and EtOAc (100 mL), the layers are separated, and the organic phase is 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 provides the title compound, mp 95-96° C.; MS (ESI−) for Cl11H14NO2Br m/z 270 (M−H)−.

Workup

  1. customthe layers are separated
  2. washthe organic phase is 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-af471824861b4c79a61fdaed4f40193e
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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