Potassium Carbonate → HCID 11789046, compound

HRID 2173154Notes

Reaction equation

HRID 2173154 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25]C=[CH:23][C:22]=2O)O1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.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>[CH3:12][C:10]1[CH:9]=[CH:8][C:3]2[C:4](=[O:5])[O:6][C:7]3[C:25]([C:2]=2[CH:11]=1)=[CH:26][CH:21]=[CH:22][CH:23]=3

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 21779704Methyl 2-bromo-4-methylbenzoate

Product 1

HCID 11789046HCID 11789046, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A sealed tube containing methyl 2-bromo-4-methylbenzoate (650 mg, 2.84 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (781 mg, 3.55 mmol) and TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) (164 mg, 0.142 mmol) was evacuated and backfilled with nitrogen before Toluene (1.29E+04 μl) and Ethanol (1290 μl) were added, followed by K2CO3 (2838 μl, 5.68 mmol). The tube was heated in the microwave for 25 minutes at 130° C. The mixture was cooled, diluted with chloroform (15 mL), washed with aqueous ammonium chloride (saturated, 10 mL), dried (Na2 SO4), filtered and the solvent was evaporated under reduced pressure. The crude product was then purified by column chromatography on silica gel Isolute Flash Si; eluting with 5-10% EtOAc/isohexane to give 9-methyl-6H-benzo[c]chromen-6-one. 1H NMR (500 MHz; CDCl3): 8.32 (d, J=8.3 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.94 (s, 1H), 7.51 (m, 1H), 7.37 (m, 3H), 2.59 (s, 3H); LC-MS (IE, m/z): 211 [M+1]+.

Workup

  1. customwas evacuated
  2. additionwere added
  3. temperatureThe mixture was cooled
  4. washwashed with aqueous ammonium chloride (saturated, 10 mL)
  5. customdried (Na2 SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude product was then purified by column chromatography on silica gel Isolute Flash Si
  9. washeluting with 5-10% EtOAc/isohexane

Sources & evidence

ORD record
ord-f638143d32fa42619212e3ff173ca2fb
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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