Sodium hydride → HCID 62142178, compound

HRID 1807422Notes

Reaction equation

HRID 1807422 reaction equation
[H-].[Na+].[CH:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[C:11]([F:17])[CH:10]=1>CN(C=O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:7][CH:3]2[CH2:6][CH2:5][CH2:4]2)=[C:11]([F:17])[CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 62142178HCID 62142178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% in oil; 1.63 g) was cautiously added to a solution of cyclobutanol (2.7 g) in DMF (12 ml). After gas evolution ceased, 4-bromo-1-bromomethyl-2-fluorobenzene (10 g) was added at 0° C. After 6 hours at room temperature, the mixture was cautiously hydrolyzed and then partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. 4-Bromo-1-cyclobutoxymethyl-2-fluorobenzene was obtained as crude product in this way.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-46c3249466114cab99aec3e8d7e484bb
Source dataset
uspto-grants-2013_01
Patent number
US08357686B2

Reaction notes

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