Hydrochloric Acid → 6-Bromo-2-methoxynaphthalene-1-carbaldehyde

HRID 1035589Notes

Reaction equation

HRID 1035589 reaction equation
[CH3:1][O:2][CH:3](Cl)Cl.[Br:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17]C)[CH:13]=2)[CH:8]=1.Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH:12]=[O:17])=[C:3]([O:2][CH3:1])[CH:11]=[CH:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 220183906-Bromo-2-methoxynaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

9.7 ml of TiCl4 (2.1 eq) and 4.2 ml of dichloromethyl methyl ether (1.1 eq) are dissolved in 20 ml of dichloromethane at 0° C. A solution of 10 g of 2-bromo-6-methoxynapthalene (1 eq) is added dropwise in such a way that the temperature does not exceed 5° C. The reaction mixture is stirred at RT over night, followed by the addition of 300 ml of 1% HCl. The organic and aqueous phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness on a rotary evaporator to obtain the desired product in quantitative yield (11 g).

Workup

  1. customdoes not exceed 5° C
  2. customThe organic and aqueous phases are separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-e641b4fbbe024538af8bf82e095b2101
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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