4-Bromoanisole → 5-Bromo-2-methoxybenzaldehyde

HRID 544326Notes

Reaction equation

HRID 544326 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][O:11]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:3]=1)[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 77304-BromoanisoleHCID 21004Methane, dichloromethoxy-

Product 1

HCID 906845-Bromo-2-methoxybenzaldehydeYield 95.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Bromoanisole (15 g., 0.08 mole) in 350 ml. of methylene chloride was cooled to 0° C. Titanium tetrachloride (30 g., 17.4 ml., 0.16 mole) was added dropwise. After 10 minutes 1,1-dichloromethyl methyl ether (12.7 g., 0.088 mole) was added dropwise and the reaction stirred for 90 minutes at 0°-10° C., then quenched into excess saturated sodium bicarbonate and methylene chloride. The organic layer was separated and combined with a further methylene chloride extract of the aqueous phase. The combined organic layers were back washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to yield 5-bromo-2-methoxybenzaldehyde (16.4 g., m.p. 107°-110° C.).

Workup

  1. customquenched into excess saturated sodium bicarbonate and methylene chloride
  2. customThe organic layer was separated
  3. extractionextract of the aqueous phase
  4. washThe combined organic layers were back washed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e9258516a8a4f3c962978c58c67b72b
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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