4-(4-Bromophenoxy)phenol → HCID 90314075, compound

HRID 2280983Notes

Reaction equation

HRID 2280983 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:27]=[CH:26][CH:25]=2)O1.O.CCOC(C)=O>COCCOC.C([O-])([O-])=O.[Na+].[Na+].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>[CH3:34][Si:33]([CH3:36])([CH3:35])[CH2:32][CH2:31][O:30][CH2:29][N:28]1[C:24]([C:2]2[CH:15]=[CH:14][C:5]([O:6][C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=3)=[CH:4][CH:3]=2)=[CH:25][CH:26]=[N:27]1

Participants

7

Reactant 3

HCID 155619664-(4-Bromophenoxy)phenolHCID 22728543Water ethylacetateHCID 447552015-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

Product 1

HCID 90314075HCID 90314075, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-(4-Bromo-phenoxy)-phenol (7.0 g, 26 mmol), and 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (9.4 g, 39 mmol) in a mixture of DME (120 mL) and 2N aqueous Na2CO3 (33 mL) is sparged with Argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.5 g, 1.3 mmol) is added to the mixture, and the mixture is heated to 100° C. After 16 hours, the mixture is cooled to room temperature and poured into water/EtOAc. The organic layer is collected, and the aqueous layer is extracted twice with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified on SiO2 (EtOAc/heptanes) to provide Intermediate A.

Workup

  1. customis sparged with Argon for 30 minutes
  2. temperaturethe mixture is cooled to room temperature
  3. customThe organic layer is collected
  4. extractionthe aqueous layer is extracted twice with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified on SiO2 (EtOAc/heptanes)

Sources & evidence

ORD record
ord-885934b039034a63b3bd3805c07d54a8
Source dataset
uspto-grants-2015_09
Patent number
US09139567B2

Reaction notes

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