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

HRID 2064774Notes

Reaction equation

HRID 2064774 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-e69bc76283db409c9e63770a5d61bb24
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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