Benzyl Bromide → HCID 67209107, compound

HRID 508666Notes

Reaction equation

HRID 508666 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15]([Br:17])[C:14]([CH3:18])=[CH:13][C:12]=3[OH:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]12([C:11]3[C:12]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:13][C:14]([CH3:18])=[C:15]([Br:17])[CH:16]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11393066HCID 11393066, compound

Product 1

HCID 67209107HCID 67209107, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(1-adamantyl)-4-bromo-5-methylphenol (6.53 g, 20.34 mmol) in acetone (65 mL) was added benzyl bromide (3.48 g, 20.34 mmol) followed by K2CO3 (3.51 g, 25.43 mmol). The mixture was stirred and heated at reflux for 24 h under argon. Acetone was removed at reduced pressure, and then 2 N HCl (80 mL) was added. The mixture was extracted with EtOAc (300 mL), and the organic layer was washed with H2O and brine and dried. After removal of solvent, the residue was purified by chromatography on a silica gel using hexane to give 7.68 g (80%) of 5-(1-adamantyl)-4-benzyloxy-2-methylphenyl bromide as a white solid, mp 138-139° C. IR 2903, 2848, 1163 cm−1; 1H NMR (CDCl3) δ 1.71 (bs, 614, AdCH2), 2.02 (bs, 3H, AdCH), 2.08 (bs, 6H, AdCH2), 2.33 (s, 3H, CH3), 5.07 (s, 2H, C6H5CH2), 6.80 (s, 1H, 3-ArH), 7.33 (s, 1H, 6-ArH), 7.3-7.5 ppm (m, 5H, C6H5).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h under argon
  3. customAcetone was removed at reduced pressure
  4. addition2 N HCl (80 mL) was added
  5. extractionThe mixture was extracted with EtOAc (300 mL)
  6. washthe organic layer was washed with H2O and brine
  7. customdried
  8. customAfter removal of solvent
  9. customthe residue was purified by chromatography on a silica gel

Sources & evidence

ORD record
ord-ed92ec23eb474464920988be01d46e9b
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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