Benzyl Bromide → HCID 58292748, compound

HRID 1798073Notes

Reaction equation

HRID 1798073 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+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

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

Product 1

HCID 58292748HCID 58292748, compoundYield 166.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-bromo-6-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde (1.8 g, 6.0 mmol) and anhydrous K2CO3 (1.66 g, 12.0 mmol) in DMF (10 mL) was slowly added 1-(bromomethyl)benzene (1.22 g, 7.2 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h before quenched by water (15 mL). The resulting mixture was further stirred for 20 min and white precipitate was collected by filtration. The solid was washed with ether and dried under high vacuum to give the title compound as a white powder (3.9 g, yield: 83%).

Workup

  1. customat 0° C
  2. custombefore quenched by water (15 mL)
  3. stirringThe resulting mixture was further stirred for 20 min
  4. filtrationwhite precipitate was collected by filtration
  5. washThe solid was washed with ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-b712288fc958486ab7ad601032ac3176
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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