Chloroform → HCID 67069112, compound

HRID 909811Notes

Reaction equation

HRID 909811 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[CH3:10].C(Cl)(Cl)Cl.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Cu+2].N1C=CC=CC=1>[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([O:8][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)=[CH:13][CH:12]=1)[CH3:10]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 115633-BromophenolHCID 2734352Boronic acid, (4-ethylphenyl)-

Product 1

HCID 67069112HCID 67069112, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

A suspension of 3-bromophenol (2.3 g, 13.3 mmol), 4-ethylphenyl boronic acid (1.0 g, 6.67 mmol), molecular sieve 4 A (14.7 g), Cu(OAc)2 (1.21 g, 6.67 mmol) and chloroform (25 mL) was stirred at room temperature for three minutes and added with triethylamine (3.6 mL) and pyridine (2.7 mL). The insolubles were filtered off with celite after the mixture was stirred for 15 hours. After the filtrate was concentrated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to obtain 1.89 g of a colorless oily title compound.

Workup

  1. filtrationThe insolubles were filtered off with celite after the mixture
  2. stirringwas stirred for 15 hours
  3. concentrationAfter the filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-35dadf438d794d2d872d2f8fb8377d5f
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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