Toluene → HCID 15183985, compound

HRID 1845150Notes

Reaction equation

HRID 1845150 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].B(O)(O)[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

Product 1

HCID 15183985HCID 15183985, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of dimethyl 5-bromoisophthalate (2.50 g, 9.15 mmol), p-tolylboronic acid (1.37 g, 10.1 mmol), toluene (50 mL), ethanol (10 mL), cesium carbonate (3.28 g, 10.1 mmol), and water (5 mL) under argon was added tetrakis(triphenylphosphine)-palladium(0) (529 mg, 0.458 mmol). The mixture was heated to reflux for 6 h, and then cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified by silica gel column (0-50% EtOAc/hexane) to yield a white solid. 1H NMR (400 MHz, CDCl3): δ 8.63 (s, 1H), 8.45 (s, 2H), 7.57 (d, 2H, J=8.0 Hz), 7.29 (d, 2H, J=8.0 Hz), 3.98 (s, 6H), 2.42 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column (0-50% EtOAc/hexane)
  6. customto yield a white solid

Sources & evidence

ORD record
ord-6afaeb1f387b4355b8ba89c20f7d2a52
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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