Potassium Carbonate → 1-[2-Hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanone

HRID 253228Notes

Reaction equation

HRID 253228 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[O:14])[CH3:13])=[C:4]([OH:15])[CH:3]=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.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>[OH:15][C:4]1[CH:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([OH:16])=[CH:18][CH:19]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:12](=[O:14])[CH3:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 668918311-(4-Bromo-2-hydroxynapthalen-1-yl)ethanone

Product 1

HCID 668908751-[2-Hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanoneYield 83.5%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-bromo-2-hydroxynapthalen-1-yl)ethanone (0.255 g, 0.96 mmol), (4-hydroxyphenyl)boronic acid (0.140 g, 1.06 mmol), Pd(PPh3)4 (0.056 g, 0.048 mmol) and potassium carbonate (0.4 g, 2.88 mmol) in water (9.7 mL) in dioxane (32.0 mL) was flushed with nitrogen, sealed and heated for 2 h in a 100° C. oil bath. The solution was cooled to room temperature and partitioned between 200 mL of 10% methanol in ethyl acetate and 100 mL saturated aqueous sodium chloride. The layers were separated and the aqueous layer was extracted (2×50 mL 10% methanol in ethyl acetate). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (SiO2, 5:1 hexanes/ethyl acetate) gave 0.223 g (83%) of 1-[2-hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanone. 1H NMR (400 MHz, d6-DMSO): 8.11 (d, 1H), 7.87 (d, 1H), 7.56 (dt, 1H), 7.33 (m, 3H), 7.07 (s, 1H), 6.99 (d, 2H), 2.89 (s, 3H); MS (EI) for C18H14O3: 279 (MH+).

Workup

  1. customwas flushed with nitrogen
  2. customsealed
  3. temperatureThe solution was cooled to room temperature
  4. custompartitioned between 200 mL of 10% methanol in ethyl acetate and 100 mL saturated aqueous sodium chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted (2×50 mL 10% methanol in ethyl acetate)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40a26978dd7b4209bee259d58964d2ec
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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