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

HRID 1693676
Notes
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Reaction equation

HRID 1693676 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[C:17]([O:19][CH3:20])=[O:18])=[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>COCCOC.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][CH:13]=[C:14]3[C:17]([O:19][CH3:20])=[O:18])=[CH:9][CH:8]=2)=[CH:32][CH:33]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 59264870Methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthalenecarboxylate

Product 1

HCID 59264859Methyl 7-(4-hydroxyphenyl)-1-naphthalenecarboxylateYield 77.7%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent
HCID 10340
Sodium Carbonate
Solvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthalenecarboxylate (1.00 g, 3.0 mmol), tetrakistriphenylphosphine palladium (142 mg, 0.12 mmol) and 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-)phenol (799 mg, 3.6 mmol) in a mixture of 1,2-dimethoxyethane (16 mL) and 2M aqueous Na2CO3 (13 mL) was heated in a 70° C. oil bath for 90 minutes. 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 (0.648 g, 77.7%). 1H NMR (DMSO-d6): 9.65 (s, 1H), 8.94 (s, 1H), 8.18-8.13 (m, 2H), 8.05 (d, J=8 Hz, 1H), 7.85 (dd, J=2, 9 Hz; 1H), 7.60 (d, J=9 Hz, 2H), 7.56-7.53 (m, 1H), 6.90 (d, J=9 Hz, 2H), 3.93 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-c62cfb4df94144ce854a9d885f0b2e1d
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158665B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes