4-Chlorophenylboronic acid → HCID 86681306, compound

HRID 1430248Notes

Reaction equation

HRID 1430248 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[O:3]1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(N(CC)CC)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:15][C:11]2[CH:10]=[C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:14]=[CH:13][CH:12]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 86681306HCID 86681306, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8471TriethylamineSolvent

Procedure

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.23 g), copper(II) acetate (0.19 g), triethylamine (0.218 g) and 4-chlorophenylboronic acid (0.237 g) were stirred at room temperature overnight. The solid was filtered off, and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (Varian, Superflash SF25-40 g column), eluting with 0-25% ethyl acetate/hexane, to provide the title compound.

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by flash chromatography (Varian, Superflash SF25-40 g column)
  4. washeluting with 0-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2831742869bf4a78b8b752e51fb7c300
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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