4-Aminophenol → Ethyl 2-(4-aminophenoxy)acetate

HRID 2174216Notes

Reaction equation

HRID 2174216 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 7748Ethyl bromoacetate

Product 1

HCID 412616Ethyl 2-(4-aminophenoxy)acetateYield 96.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

4-amino phenol (500 mg, 4.58 mmol) was suspended in acetonitrile (60 mL), the mixture cooled to 0° C. and ethyl 2-bromoacetate (0.53 mL, 4.81 mmol) added. CsCO3 (1.9 g, 10 mmol) was added in portions and the mixture stirred for 16 h, allowing to warm to RT. The mixture was filtered, the residue washed with acetonitrile and the filtrate evaporated to dryness. The crude product was suspended in DCM (˜30 mL), filtered and this filtrate evaporated to dryness to afford ethyl 2-(4-aminophenoxy)acetate (860 mg) as a dark oil that solidified on standing. 1H NMR (400 MHz, CDCl3) δ 6.79-6.74 (m, 2H), 6.66-6.60 (m, 2H), 4.53 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureto warm to RT
  2. filtrationThe mixture was filtered
  3. washthe residue washed with acetonitrile
  4. customthe filtrate evaporated to dryness
  5. filtrationfiltered
  6. customthis filtrate evaporated to dryness

Sources & evidence

ORD record
ord-8c28b1bc9fb543faacc3dd5209efad28
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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