Benzyl Bromide → HCID 67209013, compound

HRID 508676Notes

Reaction equation

HRID 508676 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][CH:10]([C:11]4=[O:18])[CH2:9]2)[CH2:15]3)[CH:7]=1.[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>[CH2:20]([O:19][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([C:11]3=[O:18])[CH2:9]1)[CH2:15]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 87310593HCID 87310593, compound

Product 1

HCID 67209013HCID 67209013, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-(5′-bromo-2′-hydroxyphenyl)-2-adamantanone (4.57 g, 14.20 mmol) in acetone (42 mL) was added benzyl bromide (2.67 g, 15.6 mmol) followed by K2CO3 (2.65 g, 19.2 mmol). The mixture was stirred at reflux for 25.7 h under argon. Acetone was removed, and 2 N HCl (60 mL) was added. The resultant mixture was extracted with EtOAc (250 mL), and the organic layer was washed with brine and dried. After removal of solvent at reduced pressure, the residue was purified on silica gel (14% to 20% EtOAc/hexane) to give 5.48 g (94%) of 5-(2′-benzyloxy-5′-bromophenyl)-2-adamantanone as a white solid, mp 163-165° C. 1H NMR (DMSO-d6) δ 1.79-2.42 (m, 13H, AdCH and AdCH2), 5.12 (s, 2H, C6H5CH2), 7.03 (d, J=8.5 Hz, 1H, 3′-ArH), 7.21 (d, J=2.4 Hz, 1H, 4′-ArH), 7.29-7.44 ppm (m, 6H, 6′-ArH, C6H5).

Workup

  1. temperatureat reflux for 25.7 h under argon
  2. customAcetone was removed
  3. addition2 N HCl (60 mL) was added
  4. extractionThe resultant mixture was extracted with EtOAc (250 mL)
  5. washthe organic layer was washed with brine
  6. customdried
  7. customAfter removal of solvent at reduced pressure
  8. customthe residue was purified on silica gel (14% to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-07f9a9a88761445f8bdbf874395d240f
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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