2-Bromophenol → Ethyl 4-(2-bromophenyloxy)but-2-enoate

HRID 963213Notes

Reaction equation

HRID 963213 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].Br[CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:16][CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 54124865Ethyl 4-(2-bromophenyloxy)but-2-enoateYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22 °C

Procedure

To an acetone solution containing pulverized anhydrous K2CO3 (5.58 g, 40.5 mmol) and 2-bromophenol (5.0 g, 28.9 mmol) was added ethyl 4-bromocrotonate (6.69 g, 34.7 mmol). The mixture was stirred at 22° C. for 5 h and filtered. The filtrate was concentrated in vacuo and treated with 5% NaHCO3 (~10 mL). The residue and aqueous phase were extracted with CH2Cl2 (3×). The combined organic extracts were dried with anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound (6.10 g, 74%) as a solid material which was used without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiontreated with 5% NaHCO3 (~10 mL)
  4. extractionThe residue and aqueous phase were extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-731d1aa040ab471d98045b57912f642c
Source dataset
uspto-grants-1998_06
Patent number
US05763444

Reaction notes

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