Water → HCID 178455776, compound

HRID 1674436Notes

Reaction equation

HRID 1674436 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18]Br)[CH2:14][CH2:13]1)[CH3:11].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([CH2:10][CH3:11])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 808792,3-DifluorophenolHCID 178455729HCID 178455729, compound

Product 1

HCID 178455776HCID 178455776, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

30 g of 2,3-difluorophenol was dissolved in 300 ml of DMF, and 56.8 g of (trans-4-ethylcyclohexyl)methyl bromide and 73.4 g of tripotassium phosphate were added thereto, and then stirred for 1 hours at 100 to 110° C. Water and toluene were added thereto, and the organic layer was fractioned while the aqueous layer was extracted with toluene. The organic layers were combined, washed with saturated saline, and then subjected to column chromatography. Then, the solvent was evaporated under reduced pressure. The residue was purified by recrystallization, to thereby obtain 37 g of 2,3-difluoro-1-(trans-4-ethylcyclohexyl)methoxybenzene.

Workup

  1. extractionwas extracted with toluene
  2. washwashed with saturated saline
  3. customThen, the solvent was evaporated under reduced pressure
  4. customThe residue was purified by recrystallization

Sources & evidence

ORD record
ord-e0c1787caa2a43669bfdfb6170530375
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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