Water → HCID 12084324, compound

HRID 1744746Notes

Reaction equation

HRID 1744746 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[F:6][C:7]1[C:19]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[F:20])[C:11]=2[CH:10]=[CH:9][C:8]=1[OH:21].C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[CH2:2]([O:21][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:17](=[C:16]([F:20])[CH:15]=[CH:14][CH:13]=3)[CH2:18][C:19]=2[C:7]=1[F:6])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 22223132HCID 22223132, compound

Product 1

HCID 12084324HCID 12084324, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

56 mmol of 1-bromobutane are added to a mixture of 36 mmol of 1,8-difluorofluoren-2-ol and 109 mmol of anhydrous potassium carbonate in 250 ml of 2-butanone (methyl ethyl ketone) and the mixture is subsequently heated to reflux for 8 h. The still hot solution is then mixed with 50 ml of water. The phases are separated, the organic phase is washed with water and saturated sodium chloride solution and dried over sodium sulfate, and the solvent is removed on a rotary evaporator. The purification is effected by filtration through aluminum oxide (neutral) using toluene as the eluent and recrystallization from heptane. 2-Butoxy-1,8-difluorofluorene is obtained.

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureto reflux for 8 h
  3. customThe phases are separated
  4. washthe organic phase is washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is removed on a rotary evaporator
  7. customThe purification
  8. filtrationis effected by filtration through aluminum oxide (neutral)
  9. customas the eluent and recrystallization from heptane

Sources & evidence

ORD record
ord-b2a77374c890483eb4eb9baea7bf7f33
Source dataset
uspto-grants-2006_03
Patent number
US07018685B2

Reaction notes

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