Benzyl Bromide → HCID 118098735, compound

HRID 708866Notes

Reaction equation

[F:1][C:2]1[C:3]([OH:21])=[C:4]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:23]([O:21][C:3]1[C:2]([F:1])=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][C:4]=1[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

17D (2.500 g, 8.33 mmol) and (bromomethyl)benzene (1.483 mL, 12.49 mmol) were dissolved in acetone (40 mL). Cesium carbonate (5.43 g, 16.65 mmol) was added, and the reaction mixture was stirred at 50° C. for 4 h. The reaction mixture was filtered, the filter cake was washed with acetone (3×25 mL). Organic fractions were combined, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (0-50% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 17E (2.789 g, 7.14 mmol, 86% yield) as a white solid. MS (ESI) m/z: 391.0 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.94 (1H, d, J=11.54 Hz), 7.77-7.90 (1H, m), 7.39 (5H, s), 5.31 (2H, br. s.), 4.25-4.50 (2H, m), 2.78 (3H, s), 1.35-1.55 (9H, m).

Workup

filtrationThe reaction mixture was filtered
washthe filter cake was washed with acetone (3×25 mL)
customthe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography (0-50% EtOAc/hexanes)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ad881c1f08664dd9886f852e64535828
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174974B2

Reaction notes

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