Benzyl Bromide → HCID 22005268, compound

HRID 324885Notes

Reaction equation

HRID 324885 reaction equation
[CH:1]([C:4]1[C:5]([CH2:24][OH:25])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[OH:23])[C:7]([CH2:13][CH2:14][CH3:15])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[Cl-].[NH4+]>[CH:1]([C:4]1[C:5]([CH2:24][OH:25])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[O:23][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]([CH2:13][CH2:14][CH3:15])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22004934HCID 22004934, compound

Product 1

HCID 22005268HCID 22005268, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of the racemic compound prepared in Example 241 (293 mg, 851 μmol), benzyl bromide (110 μL, 925 μmol), and potassium carbonate (303 mg, 2.19 mmol) in acetone (29 mL) was heated to reflux for 3 h. The mixture was diluted with saturated aqueous ammonium chloride solution (50 mL) and extracted with Et2O (3×50 mL). Silica gel chromatography (90:10 hexane/ethyl acetate) provided a colorless oil (0.369 g, 100%). 1H NMR (CDCl3, 300 MHz): δ 7.34 (s, 1H), 7.23 (m, 3H), 7.12 (m, 1H), 7.03 (m, 2H), 6.84-6.75 (m, 2H), 5.04 (d, 12.1 Hz, 1H), 4.94 (d, 12.1 Hz, 1H), 4.38 (dd, 11.4 Hz, 8.5 Hz, 1H), 4.25 (dd, 11.4 Hz, 3.3 Hz, 1H), 3.39 (sept, 6.9 Hz, 1H), 3.18 (sept, 6.9 Hz, 1H), 2.30-2.40 (m, 1H), 2.09-2.20 (m, 1H), 1.65 (dd, 8.5 Hz, 3.3 Hz, 1H), 1.26-1.34 (m, 14H), 0.72 (t, 7.4 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with Et2O (3×50 mL)

Sources & evidence

ORD record
ord-a851cede302946cca4f4063c36b3ea0c
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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