Hydrochloric Acid → 4-Bromo-2-fluoro-1-methoxymethoxy-benzene

HRID 1078027Notes

Reaction equation

HRID 1078027 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[CH3:12][O:13][CH2:14]Cl.Cl>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:12][O:13][CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 220320154-Bromo-2-fluoro-1-methoxymethoxy-benzeneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction vessel was charged with 111 g of 2-fluoro-4-bromophenol and 700 ml of DMF, and 20 g of 70% sodium hydride was added with stirring at room temperature. The mixture was stirred at room temperature for 1 hour and 56 g of methoxymethyl chloride was then added dropwise. The mixture was stirred at room temperature for 3 hours. The reaction liquid was poured into dilute hydrochloric acid and the organic layer was extracted with benzene. The benzene layer was washed with water and dried over Glauber's salt. The benzene was distilled off and the residue was distilled under reduced pressure to obtain 110 g (yield 88%) of 3-fluoro-4-methoxymethoxybromobenzene.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. customThe reaction liquid
  5. extractionthe organic layer was extracted with benzene
  6. washThe benzene layer was washed with water
  7. dry with materialdried over Glauber's salt
  8. distillationThe benzene was distilled off
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-06262777f5694aa889e26f8a9aea4785
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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