Iodoethane → Ethyl 6-bromonaphthalene-2-carboxylate

HRID 860530Notes

Reaction equation

HRID 860530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.I[CH2:16][CH3:17].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:16][CH3:17])=[O:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 1249959Ethyl 6-bromonaphthalene-2-carboxylateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-bromo-2-naphthoic acid (6.18 g, 24.6 mmol), iodoethane (19.7 mL, 38.39 g, 246.1 mmol) and Cs2CO3 (12.03 g, 36.9 mmol) in acetonitrile (200 mL) under an atmosphere was heated to reflux overnight. The resulting mixture was filtered and evaporated. The solid was dissolved in ethyl acetate and washed with water (4×), brine and dried (Mg2SO4). The mixture was filtered and evaporated to give 6.68 g of ethyl 6-bromo-2-naphthoate (97%) as a solid. 1H NMR (500 MHz; CDCl3): δ 1.45 (t, J=7.0 Hz, 3H); 4.44 (q, J=7.0 Hz, 2H); 7.61 (dd, J1=2.0 Hz, J2=9.0 Hz, 1H); 7.79 (d, J=8.5 Hz, 1H); 7.82 (d, J =9.0 Hz, 1H); 8.00–8.11 (m, 2H); 857 (brs, 1H),

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe resulting mixture was filtered
  4. customevaporated
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. washwashed with water (4×), brine
  7. dry with materialdried (Mg2SO4)
  8. filtrationThe mixture was filtered
  9. customevaporated

Sources & evidence

ORD record
ord-0c1d0a373a8445c58ce7fcf75044534d
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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