3-Hydroxybenzaldehyde → HCID 15058630, compound

HRID 1371937Notes

Reaction equation

HRID 1371937 reaction equation
Br[CH2:2][CH2:3][F:4].[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[F:4][CH2:3][CH2:2][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromide

Product 1

HCID 15058630HCID 15058630, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Combine 1-bromo-2-fluoroethane (4.575 g; 36.0 mmol), 3-hydroxybenzaldehyde (4.103 gm; 33.60 mmol), and K2CO3 (7.05 gm; 51.0 mmol) in 2-butanone (100 mL) and reflux. After 18 hour cool the mixture to ambient temperature, concentrate, and partition between 100 mL of water and 100 mL of dichloromethane. Separate the layers and extract the aqueous layer with dichloromethane (2×75 mL). Combine the organic layers and wash sequentially with brine (2×150 mL), 1 M NaOH (2×100 mL), NaHCO3 (saturated, 100 mL), and brine (150 mL), dried (MgSO4), concentrate, and chromatograph on silica gel (0–25% diethyl ether in hexanes) to give the title compound.

Workup

  1. concentrationconcentrate
  2. custompartition between 100 mL of water and 100 mL of dichloromethane
  3. customSeparate the layers
  4. extractionextract the aqueous layer with dichloromethane (2×75 mL)
  5. washCombine the organic layers and wash sequentially with brine (2×150 mL), 1 M NaOH (2×100 mL), NaHCO3 (saturated, 100 mL), and brine (150 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-04acda6cf37743dbab01895e1cc51733
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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