4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Methyl 7-(4-hydroxyphenyl)-2-naphthalenecarboxylate

HRID 646028Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14]2)=[CH:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)O1>C(COC)OC.C([O-])([O-])=O.[Na+].[Na+]>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14]3)=[CH:9][CH:8]=2)=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-2-naphthalenecarboxylate (100 mg, 0.3 mmol), tetrakistriphenylphosphine palladium (14 mg, 0.012 mmol) and 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-) phenol (79 mg, 0.36 mmol) in a mixture of dimethoxyethane (1.6 mL) and 2 M aqueous Na2CO3 (1.3 mL) was heated in a 70° C. oil bath for one hour. The solution was partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by chromatography on silica gel, (hexane to 3:7 ethyl acetate:hexanes) to provide the title compound (0.085 g, 95.5% as 0.20 ethyl acetate). 1H NMR (DMSO-d6): δ 9.64 (s, 1H), 8.65 (s, 1H), 8.31 (s, 1H), 8.03-7.99 (m, 2H), 7.93-7.90 (m, 2H), 7.66 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 3.90 (s, 3H).

Workup

customThe solution was partitioned between ethyl acetate and water
dry with materialThe organic layer was dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by chromatography on silica gel, (hexane to 3:7 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-727903f00dbc4353aa3fd1bce37b1699
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705028B2

Reaction notes

Loading…