Sodium Carbonate → Methyl 6-(4-hydroxyphenyl)-2-naphthoate

HRID 646024Notes

Reaction equation

HRID 646024 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]3)=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 19834505Methyl 6-(4-hydroxyphenyl)-2-naphthoate

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 6-bromo-2-naphthoate (150 mg, 0.57 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (150 mg, 0.68 mmol), and 2.0 M Na2CO3 (1.10 mL, aq) in dimethoxyethane (5 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (14 mg, 0.02 mmol) and the mixture stirred at 70° C. for 20 min. The mixture was diluted with 25 mL of EtOAc then filtered through a plug of Celite and silica gel. The filtrate was washed with H2O, then brine, dried over Na2SO4, then concentrated and purified by silica gel chromatography (40 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes) to give methyl 6-(4-hydroxyphenyl)-2-naphthoate as a beige solid (55 mg, 35%.) 1H NMR (DMSO-d6): δ 9.67 (s, 1H), 8.60 (s, 1 H), 8.17-8.13 (m, 2 H), 8.02 (d, J=9 Hz, 1 H), 7.95 (d, J=9 Hz, 1 H), 7.87 (d, J=9 Hz, 1H), 7.67 (d, J=8 Hz, 2H), 6.89 (d, J=8 Hz, 2H), 3.89 (s, 3H). ESI-LCMS m/z 279 (M+H)+.

Workup

  1. filtrationthen filtered through a plug of Celite and silica gel
  2. washThe filtrate was washed with H2O
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (40 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes)

Sources & evidence

ORD record
ord-a86e8001ae304cc1be9047915ca05694
Source dataset
uspto-grants-2010_04
Patent number
US07705028B2

Reaction notes

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