Sodium hydride → HCID 62142178, compound

HRID 1695526Notes

Reaction equation

HRID 1695526 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-7dec8d37c7c746bbae304f3af2dfee65
Source dataset
uspto-grants-2012_04
Patent number
US08163741B2

Reaction notes

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