Dichloromethane → HCID 12387307, compound

HRID 346045Notes

Reaction equation

HRID 346045 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[O:13].[Br:14]Br.C(Cl)Cl>C(OCC)C>[Br:14][CH:7]1[C:6](=[O:13])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 46121686-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 12387307HCID 12387307, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-methoxy-4-chromanone (35 g) in ethyl ether (1.6 liters) at 5°-10° C. was added dropwise over 30 minutes 10.6 ml of bromine. The mixture was stirred at 5°-10° C. for 30 minutes and then allowed to warm to room temperature. After 2 hours tlc (CH2Cl2) indicated formation of less polar products and only a trace of starting material remaining. The reaction mixture was washed with water (1 liter), saturated NaHCO3 (500 ml), and brine (500 ml), dried over MgSO4, and concentrated in vacuo to a yellow solid. The crude product was purified by silica gel flash column chromatography on 2.4 Kg fine silica gel, eluting with a gradient system consisting of 3:1 hexanes/dichloromethane followed by 2:1 hexanes/dichloromethane and finally 30% hexanes/dichloromethane. This afforded title product as a yellow solid in 80% yield.

Workup

  1. washThe reaction mixture was washed with water (1 liter), saturated NaHCO3 (500 ml), and brine (500 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo to a yellow solid
  4. customThe crude product was purified by silica gel flash column chromatography on 2.4 Kg fine silica gel
  5. washeluting with a gradient system

Sources & evidence

ORD record
ord-1f0640ddf9f2452f8c3b8b6a07ce3046
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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