Ethyl bromoacetate → Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate

HRID 1940485Notes

Reaction equation

HRID 1940485 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[O:8][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 13752803Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 5-fluoro-2-nitrophenol (100.0 gm, 0.64 mol), ethyl bromoacetate (77.6 mL, 116.9 gm, 0.78 mol) and K2CO3 (175.9 gm, 1.27 mol) in acetonitrile (800 mL), under N2, was heated to reflux for 1 hour. The reaction mixture was filtered and the filtrate was washed with brine (200 mL), dried (MgSO4) and evaporated to dryness to give the title compound of Step A, Example 3, as an orange solid (150.0 gm), 97%; m.p. 37°-39° C.; 1H NMR δ: 1.28-1.32 (t,3H), 4.23-4.29 (m,2H), 4.77 (s,2H), 6.64-6.68 (d,1H), 6.79-6.83 (t,1H), 7.96-8.01 (q,1H).

Workup

  1. temperatureunder N2, was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. washthe filtrate was washed with brine (200 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8251cc04377a4a37a81e9ab34a8ca5c1
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

Loading…