3-Fluorophenol → HCID 67219630, compound

HRID 1011473Notes

Reaction equation

HRID 1011473 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 NaHCO3 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 NaHCO3 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-1b15b4448b3f430489d5f886fd5d8631
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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