3-Fluorophenol → HCID 67219630, compound

HRID 1921256Notes

Reaction equation

HRID 1921256 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]12([C:15](Cl)=[O:16])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.[F:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.CCCCCCC.C1(C)C=CC=CC=1>ClCCCl>[C:5]12([C:15]([C:24]3[CH:23]=[CH:22][C:21]([OH:25])=[CH:20][C:19]=3[F:18])=[O:16])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

6

Reactant 4

HCID 97433-FluorophenolHCID 989151-Adamantanecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22263336Toluene heptane

Product 1

HCID 67219630HCID 67219630, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

To a mixture of AlCl3 (45 g, 0.337 mol) in 1,2-dichloroethane (DCE, 250 ml) at 0° C. was added 1-adamantyl carbonyl chloride (36.6 g, 0.228 mol) in DCE (150 ml). 3-fluorophenol (21 g, 0.183 mol) in DCE (100 ml) was added slowly at 0° C. The reaction was followed by TLC (heptane/toluene 50/50). The mixture was poured onto HCl 2N, extracted with AcOEt, washed with Nat-HCO3 and brine, dried over Na2SO4, filtered and concentrated under vacuum. Purification by flash chromatography (heptane/toluene 8/2) gave 27 g of 1-adamantyl (2-fluoro-4-hydroxyphenyl)methanone (48% as solid).

Workup

  1. additionThe mixture was poured onto HCl 2N
  2. extractionextracted with AcOEt
  3. washwashed with Nat-HCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash chromatography (heptane/toluene 8/2)

Sources & evidence

ORD record
ord-761aa30bf98b42af9984997f115941d5
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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