Dichloromethane → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one

HRID 1797210Notes

Reaction equation

HRID 1797210 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1)=[O:3].C(Cl)Cl.CCN(CC)CC.[BH3:21].[OH:22][C:23]([C:26]([OH:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)C>[CH3:24][C:23]1([CH3:25])[C:26]([CH3:28])([CH3:27])[O:29][B:21]([C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)[O:22]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 178419189HCID 178419189, compound

Product 1

HCID 27605961-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-oneYield 64%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 3283Diethyl EtherSolvent

Procedure

4-Iodo acetophenone (10.00 g, 40.64 mmol), PdCl2(dppf).CH2Cl2 (1.00 g, 1.22 mmol) dry dioxane (160 mL) and Et3N (17.0 mL, 121.96 mmol) were combined in a dry flask which had been purged with N2 several times. Pinacol borane (8.80 mL, 60.96 mmol) was added and the reaction mixture was heated at reflux for 4 h then cooled to ambient temperature, poured into Diethyl ether (250 mL) and extracted with H2O and washed with brine. The Diethyl ether was dried (MgSO4), filtered and the filtrate concentrated in vacuo. Purification by gradient chromatography on silica (hexane, 5% EtOAc/hexane) followed by recrystallization (hexane) gave 6.4 g (64%) of the intermediate title compound as a white powder.

Workup

  1. customwhich had been purged with N2 several times
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 4 h
  4. extractionextracted with H2O
  5. washwashed with brine
  6. dry with materialThe Diethyl ether was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification by gradient chromatography on silica (hexane, 5% EtOAc/hexane)
  10. customfollowed by recrystallization (hexane)

Sources & evidence

ORD record
ord-157d29ffa61d4af4ad164d4c83a9bf37
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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