Phenol → 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

HRID 266201Notes

Reaction equation

HRID 266201 reaction equation
[CH:1]1([Br:6])[CH2:5]C[CH2:3][CH2:2]1.[C:7]1(O)[CH:12]=CC=C[CH:8]=1.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH2:20]([O:22][CH2:23][CH3:24])[CH3:21]>C(#N)C.CCCCCC>[CH:20]1([O:22][C:23]2[CH:5]=[C:1]([Br:6])[CH:2]=[CH:3][C:24]=2[O:17][CH3:14])[CH2:12][CH2:7][CH2:8][CH2:21]1

Participants

7

Reactant 4

HCID 996PhenolHCID 3283Diethyl EtherHCID 8728Bromocyclopentane2×HCID 11430Potassium Carbonate2×

Product 1

HCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

Cyclopentyl bromide (37 mL, 0.345 mol) was added to a slurry of the phenol (50 g, 0.246 mol) and potassium carbonate (17 g, 0.123 mol) in acetonitrile (500 mL) at reflux temperature. After two hours, cyclopentyl bromide (13.2 mL, 0.123 mol) and potassium carbonate (8.5 g, 0.062 mol) were added to complete the reaction (1 hour). Reaction progress was monitored by TLC (50% ethyl ether in hexane). The suspension was filtered. The filtered material was washed with ethyl acetate (2×100 mL). The filtrates were combined, concentrated and distilled under vacuum (0.1 mm, 140° C.°145° C.) to yield 65.62 g (0.242 mol, 98%) of product,

Workup

  1. temperatureat reflux temperature
  2. customthe reaction (1 hour)
  3. customReaction progress
  4. filtrationThe suspension was filtered
  5. washThe filtered material was washed with ethyl acetate (2×100 mL)
  6. concentrationconcentrated
  7. distillationdistilled under vacuum (0.1 mm, 140° C.°145° C.)

Sources & evidence

ORD record
ord-8abaebbb46e1445bad126d16a9e0e76a
Source dataset
uspto-grants-1997_07
Patent number
US05650444

Reaction notes

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