Water → HCID 59129194, compound

HRID 1964241Notes

Reaction equation

HRID 1964241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.O>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:6][C:7]=1[Br:22]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58841079Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylate

Product 1

HCID 59129194HCID 59129194, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 1-(4-aminophenyl)cyclopropanecarboxylate (10.38 g, 0.05 mol) in acetonitrile (200 mL) was added NBS (9.3 g, 0.05 mol) at room temperature. The mixture was stirred overnight. Water (200 mL) was added. The organic layer was separated and the aqueous phase was extracted with EtOAc (80 mL×3). The organic layers were dried with anhydrous Na2SO4 and evaporated to give methyl 1-(4-amino-3-bromophenyl)cyclopropanecarboxylate (10.6 g, 78%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=2.0 Hz, 1 H), 7.08 (dd, J=1.6, 8.4 Hz, 1H), 6.70 (d, J=8.4 Hz, 1 H), 3.62 (s, 3 H), 1.56-1.54 (m, 2 H), 1.14-1.11(m, 2 H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (80 mL×3)
  3. dry with materialThe organic layers were dried with anhydrous Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-cfc58497958b48ed8bc403d7d95c4829
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

Loading…