Sodium Carbonate → 7-(m-Tolyl)chroman-4-one

HRID 594772Notes

Reaction equation

HRID 594772 reaction equation
Br[C:2]1C=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH3:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=[O:24].[Na+].[Na+]>O1CCOCC1.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>[CH3:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[O:24])[CH2:5][CH2:6][O:7][C:8]=3[CH:12]=2)[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 101050696-Bromo-1-tetralone

Product 1

HCID 1185977737-(m-Tolyl)chroman-4-oneYield 96%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol), 3-methylbenzeneboronic acid (1.8 g, 13.2 mmol), Na2CO3 (2.8 g, 26.4 mmol) in dioxane (40 mL) and water (2 mL) was added Pd(PPh3)4 (509 mg, 0.4 mmol) at rt under N2. The reaction was stirred at 100° C. overnight. The reaction was filtered and concentrated. Purification by silica gel chromatography (PE:EtOAc=12:1) gave 2.0 g (96%) of the title compound as a white oil. 1H NMR (300 MHz, CDCl3): δ 2.44 (3H, s), 2.86 (2H, t, J=6.6 Hz), 4.59 (2H, t, J=6.6 Hz), 7.20-7.29 (3H, m), 7.36-7.44 (3H, m), 7.87 (1H, d, J=8.1 Hz). [M+H] Calc'd for C16H14O2, 239. Found, 239.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (PE:EtOAc=12:1)

Sources & evidence

ORD record
ord-3be5827107f64c0bac0281850ec16183
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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