Benzyl Bromide → HCID 58292748, compound

HRID 1798262Notes

Reaction equation

HRID 1798262 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[C:6]([OH:17])[C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:24]([O:17][C:6]1[CH:7]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:9]=[C:2]([Br:1])[C:3]=1[CH:4]=[O:5])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58292840HCID 58292840, compound

Product 1

HCID 58292748HCID 58292748, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-6-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.00 g, 10.0 mmol) in DMF (20 mL) was added K2CO3 (2.76 g, 20.0 mmol) followed by benzyl bromide (1.43 mL, 12.0 mmol) at 0° C. The suspension was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=6:1) to give the title compound (3.79 g, 97%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 10.39 (s, 1H), 7.47-7.33 (m, 5H), 6.98 (d, J=2.1 Hz, 1H), 6.70 (d, J=2.1 Hz, 1H), 5.47-5.45 (m, 1H), 5.16 (s, 2H), 3.80-3.78 (m, 1H), 3.66-3.62 (m, 1H), 1.88-1.55 (m, 6H).

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-bd5525a34f054093a7d9c1798cd696cb
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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