Water → 2-Bromo-4-cyclopentylaniline

HRID 383395Notes

Reaction equation

HRID 383395 reaction equation
[CH:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:20])C(=O)C1.O>CN(C=O)C>[Br:20][C:11]1[CH:12]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 118160214-Cyclopentylaniline

Product 1

HCID 593949932-Bromo-4-cyclopentylanilineYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Cyclopentylaniline (210 mg, 1.30 mmol) was dissolved in cold (0° C.) DMF (8 mL) and treated with NBS (232 mg, 1.30 mmol). The reaction was stirred at 0° C. for 5 min and then warmed to room temperature for 1 h. The reaction mixture was poured into water (40 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (0-50% ethyl acetate/hexanes) yielded 2-bromo-4-cyclopentylaniline (251 mg, 80% yield). LC/MS m/z 242.0 [M+H]+.

Workup

  1. temperaturewarmed to room temperature for 1 h
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic extracts dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-747b200e24e2477cb5d8590858f72b1f
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

Loading…