Potassium Carbonate → HCID 68878543, compound

HRID 1454230Notes

Reaction equation

HRID 1454230 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[OH:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1>CC#N.CCOC(C)=O.O>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[O:17][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 68427594HCID 68427594, compound

Product 1

HCID 68878543HCID 68878543, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (5-bromo-2-hydroxy-benzyl)-methyl-carbamic acid tert-butyl ester (1.0 g, 3.2 mmol), K2CO3 (655 mg, 4.74 mmol), and 4-bromomethyl-1,2-dichloro-benzene (1.14 g, 4.74 mmol) in CH3CN (6.3 mL) was heated at 90° C. overnight. The mixture was then cooled to rt, diluted with EtOAc and water, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. Purification by FCC (EtOAc/hexanes) gave the desired product (1.49 g, 99%). 1H NMR (CDCl3, mixture of rotamers): 7.49 (d, J=1.9, 1H), 7.46 (d, J=7.8, 1H), 7.31 (dd, J=8.7, 2.0, 1H), 7.28-7.22 (m, 2H), 6.73 (d, J=8.6, 1H), 5.00 (s, 2H), 4.52-4.38 (m, 2H), 2.90-2.80 (m, 3H), 1.52-1.39 (m, 9H).

Workup

  1. temperatureThe mixture was then cooled to rt
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by FCC (EtOAc/hexanes)

Sources & evidence

ORD record
ord-e47b8fd21fbe4cb5b4ce9ff5194f4bee
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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