Sodium Carbonate → HCID 9949633, compound

HRID 1018113Notes

Reaction equation

HRID 1018113 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH3:14])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1.[C:15]([O-:18])([O-])=[O:16].[Na+].[Na+].BrBr>[Fe].C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1([CH3:14])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:3]#[C:4][C:13]3[CH:8]=[CH:9][C:10]([C:15]([OH:18])=[O:16])=[CH:11][CH:12]=3)[CH:12]=2)[O:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 18406103HCID 18406103, compound

Product 1

HCID 9949633HCID 9949633, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.00 g (10.4 mmol) of 4-methoxymethyl-4-methyl-chroman was dissolved in 25 ml of abs. CH2Cl2 and treated with a catalytic amount of Fe-powder and Na2CO3. After cooling to 0° C., 1.21 m of bromine (1.1 eq.) was added and the mixture kept for 0.6 h at this temperature. Pouring onto crushed ice, extraction with diethylether, washing the organic phase with water, drying it over magnesium sulfate, filtration and evaporation of the solvents, and ensuing flash chromatography over SiO2 (hexane/ethylacetate 95/5) yielded 1.676 g of pure title compound as colorless oil (GC>95%).

Workup

  1. additionPouring
  2. customonto crushed
  3. extractionice, extraction with diethylether
  4. washwashing the organic phase with water
  5. customdrying it
  6. filtrationover magnesium sulfate, filtration and evaporation of the solvents

Sources & evidence

ORD record
ord-ffa4f2ba9ca945d4a236b0801b8bccae
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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