Ethanol → HCID 58449378, compound

HRID 2278714Notes

Reaction equation

HRID 2278714 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](I)[CH:10]=1)[C:5]([OH:7])=[O:6].B(O)(O)[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1.C(O)C.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:10]=1

Participants

8

Reactant 6

HCID 702EthanolHCID 962WaterHCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 58449378HCID 58449378, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

A pressure vial was charged with 3-bromo-5-iodo-benzoic acid (7.60 g, 23.2 mmol), p-tolylboronic acid (3.16 g, 23.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.34 g, 1.16 mmol), cesium carbonate (8.33 g, 25.6 mmol), toluene (99.0 mL, 930 mmol), ethanol (27.1 mL, 465 mmol) and water (12.6 mL, 697 mmol) and the reaction stirred at 85° C. over nights. The reaction mixture was filtered over celite and the solvent removed to get the crude product as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. customthe solvent removed

Sources & evidence

ORD record
ord-bed884a083644b15b3a3ca72c74dbdd7
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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