Allyl bromide → Ethyl 4-fluoro-3-(2-propen-1-yloxy)benzoate

HRID 560316Notes

Reaction equation

HRID 560316 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH:9]=[CH2:10].[CH2:11]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([OH:22])[CH:16]=1)[CH3:12]>CC(C)=O>[CH2:11]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH2:10][CH:9]=[CH2:8])[CH:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18007712Ethyl 4-fluoro-3-hydroxybenzoate

Product 1

HCID 66998735Ethyl 4-fluoro-3-(2-propen-1-yloxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (96.9 mmol) and 3-bromo-1-propen (64.6 mmol) are added to a solution of 4-fluoro-3-hydroxy-benzoic acid ethyl ester (32.3 mmol) in acetone (50 mL). The mixture is heated to reflux for 16 h, filtered and cooled to RT. The solvents are removed in vacuo to give the desired product which is used without further purification. LC-MS: tR=1.01 min; [M+CH3CN+H]+=266.0.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-b0f29086079d4af2aca10cfe0353505d
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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