Monobenzone → HCID 71227448, compound

HRID 2280984Notes

Reaction equation

HRID 2280984 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](Cl)=[N:12][CH:13]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C(OCC)(=O)C>CN(C=O)C>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][C:11]2[CH:10]=[CH:9][C:8]([Br:7])=[CH:13][N:12]=2)=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7638MonobenzoneHCID 27344145-Bromo-2-chloropyridineHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 71227448HCID 71227448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Potassium tert-butoxide (7 g, 62 mmol) is added to a solution of 5-bromo-2-chloro-pyridine (10 g, 52 mmol) and 4-benzyloxy-phenol (10.4 g, 52 mmol) in DMF (104 mL). The mixture is heated to 110° C. for 3.5 hours then cooled. The solution is then poured into water/ethyl acetate, and the organic layer is collected. The aqueous layer is extracted twice with EtOAc, and the combined organic layers are washed with brine. The organic layer is then dried over Na2SO4, filtered and concentrated. The resulting residue is purified on SiO2 (EtOAc/heptanes) to provide Intermediate D.

Workup

  1. temperaturethen cooled
  2. customthe organic layer is collected
  3. extractionThe aqueous layer is extracted twice with EtOAc
  4. washthe combined organic layers are washed with brine
  5. dry with materialThe organic layer is then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified on SiO2 (EtOAc/heptanes)

Sources & evidence

ORD record
ord-ae84f7a4038d46dda5a9545edfaee404
Source dataset
uspto-grants-2015_09
Patent number
US09139567B2

Reaction notes

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