p-Toluenesulfonic acid → 2-Bromo-4-fluoro-1-(methoxymethoxy)benzene

HRID 252230Notes

Reaction equation

HRID 252230 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:21][O:22][CH2:23]OC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:21][O:22][CH3:23]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8020DimethoxymethaneHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 220325852-Bromo-4-fluoro-1-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-4-fluoro-phenol (1 g, 5.23 mmol) in CH2Cl2 (120 mL) was added p-toluenesulphonic acid (0.07 g, mmol), dimethoxymethane (2.31 mL, 26.15 mmol) and the resulting mixture was heated under reflux for 16 h under a soxhlett apparatus charged with freshly dried molecular 4 Å sieves. The reaction was allowed to warm to room temperature and washed with 2M sodium hydroxide (100 mL) then dried (Na2SO4), filtered and the solvent was evaporated under vacuum to give title compound as an oil: 0.567 g, 46%. 1H-NMR (CDCl3, 300 MHz) δ7.31 (dd, 1H, J=2.9, 7.9 Hz, ArH), 7.13 (dd, 1H, J=4.9, 9.1 Hz, ArH), 6.98 (m, 1H, ArH), 5.21 (s, 2H, —OCH2O—), 3.54 (s, 3H, —OCH3)

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 16 h under a soxhlett apparatus
  3. additioncharged with freshly dried molecular 4 Å
  4. washwashed with 2M sodium hydroxide (100 mL)
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-3cfc19f41b774540bdf7178be25e68e1
Source dataset
uspto-grants-2011_01
Patent number
US07868032B2

Reaction notes

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