(2,4-Dichlorophenyl)boronic acid → 1-(2,4-Dichlorophenyl)-3-methylnaphthalen-2-ol

HRID 514028Notes

Reaction equation

HRID 514028 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH3:23])[C:14]=1[OH:24]>C([O-])([O-])=O.[K+].[K+].COCCOC.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>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH3:23])[C:14]=1[OH:24]

Participants

6

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 671260591-Bromo-3-methylnaphthalen-2-ol

Product 1

HCID 671261341-(2,4-Dichlorophenyl)-3-methylnaphthalen-2-olYield 98.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-dichlorophenylboronic acid (1.0 g), tetrakis(triphenylphosphine)palladium(0) (300 mg), 1-bromo-3-methyl-naphthalen-2-ol (5B, 625 mg) in K2CO3 (2 M, 5.3 mL) and DME (26 mL) was degassed with argon and sealed in a Schlenk tube. The reaction was heated to 80° C. for 75 minutes, then cooled to room temperature. The reaction was diluted with EtOAc and filtered through a pad of silica gel. The silica was washed with EtOAc and the combined organics were concentrated. The crude residue was purified by flash column chromatography (0-18% EtOAc in hexanes) to yield 784 mg of desired product.

Workup

  1. customwas degassed with argon
  2. customsealed in a Schlenk tube
  3. temperaturecooled to room temperature
  4. additionThe reaction was diluted with EtOAc
  5. filtrationfiltered through a pad of silica gel
  6. washThe silica was washed with EtOAc
  7. concentrationthe combined organics were concentrated
  8. customThe crude residue was purified by flash column chromatography (0-18% EtOAc in hexanes)

Sources & evidence

ORD record
ord-692da5c59ee94ed093519f3ffacb053d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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