Benzyl Bromide → HCID 67209097, compound

HRID 508673Notes

Reaction equation

HRID 508673 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([O:18][CH3:19])[C:12]=3[OH:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]12([C:11]3[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([O:18][CH3:19])[C:12]=3[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 85724205HCID 85724205, compound

Product 1

HCID 67209097HCID 67209097, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(1-adamantyl)-4-bromo-6-methoxyphenol (3.30 g, 79.78 mmol) in acetone (32 mL) was added benzyl bromide (1.72 g, 10.07 mmol) followed by K2CO3 (1.69 g, 12.2 mmol). This mixture was stirred and heated at reflux temperature for 20.75 h under argon. Acetone was removed at reduced pressure, and 2 N HCl (30 mL) was added. The mixture was extracted with EtOAc (150 mL), and the organic layer was washed with brine and dried. After removal of solvent at reduced pressure, the residue was crystallized (MeOH) to give 3.99 g (95%) of 3-(1-adamantyl)-4-benzyloxy-5-methoxyphenyl bromide as a white solid, mp 89-91° C. IR 2901, 2847, 1444, 1201 cm−1; 1H NMR (CDCl3) δ 1.67 (m, 6H, AdCH2), 2.00 (bs, 3H, AdCH), 2.05 (bs, 6H, AdCH2), 3.85 (s, 3H, OCH3), 5.07 (s, 2H, C6H5CH2), 6.96 (d, J=2.3 Hz, 1H, 6-ArH), 7.01 (d, J=2.3 Hz, 1H, 2-ArH), 7.30-7.52 ppm (m, 5H, C6H5).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 20.75 h under argon
  3. customAcetone was removed at reduced pressure, and 2 N HCl (30 mL)
  4. additionwas added
  5. extractionThe mixture was extracted with EtOAc (150 mL)
  6. washthe organic layer was washed with brine
  7. customdried
  8. customAfter removal of solvent at reduced pressure
  9. customthe residue was crystallized (MeOH)

Sources & evidence

ORD record
ord-1664b74d9fd34a9d96acbefc6903ed19
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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