Calcium Carbonate → 1,4-Dimethoxy-3-bromo-2-hydroxymethylnaphthalene

HRID 1527702Notes

Reaction equation

HRID 1527702 reaction equation
[Br:1][C:2]1[C:11]([CH2:12]Br)=[C:10]([O:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH3:17].C([O-])([O-])=[O:19].[Ca+2]>COCCOC.O>[Br:1][C:2]1[C:11]([CH2:12][OH:19])=[C:10]([O:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH3:17]

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 104061942-Bromo-3-bromomethyl-1,4-dimethoxynaphthalene

Product 1

HCID 105180901,4-Dimethoxy-3-bromo-2-hydroxymethylnaphthaleneYield 105%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following a modified procedure of Smith et al.,25 dibromide 36 (1.73 g, 4.80 mmol) was dissolved in 1,2-dimethoxyethane (50.0 mL), and then added to CaCO3 (2.50 g, 25.0 mmol) in H2O (50.0 mL) at room temperature. The reaction was heated under reflux for TIME and then cooled to room temperature. The reaction was extracted with EtOAc (75.0 mL), and the organic layers are washed with brine. The organic layer was dried over MgSO4 and filtered. The resulting pink solid was then purified by flash column chromatography (1:3 EtOAc:hexanes) to provide 37 (1.49 g, 5.01 mmol, 105%) as a pink solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for TIME
  3. extractionThe reaction was extracted with EtOAc (75.0 mL)
  4. washthe organic layers are washed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customThe resulting pink solid was then purified by flash column chromatography (1:3 EtOAc:hexanes)

Sources & evidence

ORD record
ord-e2499e625e1f4e70b1aa8ea0966629e4
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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