Water → HCID 13553296, compound

HRID 1722320Notes

Reaction equation

HRID 1722320 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([CH2:14]Br)[CH:8]=1.O.CCOCC>CN(C=O)C>[C:1]([O:4][CH2:14][C:9]1[CH:8]=[C:7]([Br:6])[CH:12]=[CH:11][C:10]=1[F:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 13553296HCID 13553296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous sodium acetate (1.65 g, 20 mmol) was added to a solution of the compound (1a) (3 g, 14.6 mmol) in DMF (25 mL) and the reaction mixture was stirred under N2 on a steam bath for 11 hours. The reaction mixture was cooled and distributed between H2O (200 mL) and Et2O (100 mL). The organic layer was separated and washed with H2O (3×100 mL), dried, filtered and evaporated, leaving the compound (1b) as a nearly colorless oil; NMR 2.08 (3H, s), 5.08 (2H, s), 6.7-7.9 (3H, m).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with H2O (3×100 mL)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3b87c83d8e8c42ddb4afaaca0ea3c7fa
Source dataset
uspto-grants-1989_08
Patent number
US04855321

Reaction notes

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