Potassium Carbonate → HCID 68615140, compound

HRID 1841584Notes

Reaction equation

HRID 1841584 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CC(C)=O>[C:1]([O:5][C:6](=[O:16])[N:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])=[CH:13][CH:14]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 54592515(4-Hydroxy-phenyl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 68615140HCID 68615140, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 6.56 g (29.4 mmol) of (4-Hydroxy-phenyl)-methyl-carbamic acid tert-butyl ester dissolved in 250 ml of acetone was treated with 12.2 g (88.1 mmol) of K2CO3 and 13.4 ml (88.1 mmol) of 1,6-dibromohexane. The suspension was heated under reflux overnight, cooled, filtered and concentrated. Purification by flash chromatography on silica gel with toluene/EtOAc (95:5) as eluent yielded 9.79 g (86%) of [4-(6-Bromo-hexyloxy)-phenyl]-methyl-carbamic acid tert-butyl ester, MS: 386 (MH+, 1Br).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel with toluene/EtOAc (95:5) as eluent

Sources & evidence

ORD record
ord-b3c7423172e44b07814dae21d1038fa9
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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