Dimethoxymethane → 2-Bromo-4-fluoro-1-(methoxymethoxy)benzene

HRID 1622076Notes

Reaction equation

HRID 1622076 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O:11][CH2:12]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12]

Participants

6

Reactant 4

HCID 8020DimethoxymethaneHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 220325852-Bromo-4-fluoro-1-(methoxymethoxy)benzeneYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-fluorophenol (25.0 g, 0.13 mol) was dissolved in dry dichloromethane (100 mL) and dimethoxymethane (115 mL, 1.30 mol). Phosphorus pentoxide (110.8 g, 0.39 mol) was added portion-wise to the solution such that the reaction temperature remained below 40° C. The mixture was stirred vigorously at room temperature for 2 hours and then carefully poured into 1N aqueous NaOH (50 mL). The organic layer was separated, washed with water and then brine, dried over anhydrous MgSO4, filtered and concentrated to give 2-bromo-4-fluoro-1-methoxymethoxy-benzene (30.1 g) as a colorless oil.

Workup

  1. customremained below 40° C
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine, dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6afa172894444df096ef8fa770b5fa72
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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