Iodine → HCID 59711803, compound

HRID 2222178Notes

Reaction equation

HRID 2222178 reaction equation
[Mg].II.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[O:13]1[CH2:19][C:18](=[O:20])[CH2:17][O:16][CH2:15][CH2:14]1>C1COCC1>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:18]2([OH:20])[CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:19]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 77304-BromoanisoleHCID 5462224MagnesiumHCID 468563761,4-Dioxepan-6-one

Product 1

HCID 59711803HCID 59711803, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Magnesium (1.27 g, 0.053 mol), dried in an oven for 1 hr at 75° C., was stirred with THF (125 mL) in a 500 mL three-necked flask at reflux. A crystal of iodine was added followed by a solution of 4-methoxybromobenzene in THF (50 mL), added dropwise over 15 min. After the addition of 10 mL of the solution the reaction initiated. After complete addition of the solution, the reaction mixture was heated at reflux for 2 hrs. The resulting grey solution was cooled to 0° C. and a solution of 1,4-dioxepan-6-one (prepared as described in U.S. Pat. No. 4,410,354) (5.08 g, 0.044 mol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight then evaporated. The residue was acidified to pH=1 with 1N HCl and extracted with ether (2×250 mL). The ether extracts were washed with water, dried (MgSO4), filtered and concentrated to give a sticky brown solid (9.45 g). This was purified by column chromatography on silica gel eluting with ethyl acetate-hexanes. The relevant fractions were concentrated to give the desired product (6.21 g, 63%).

Workup

  1. temperatureat reflux
  2. additionadded dropwise over 15 min
  3. additionAfter complete addition of the solution
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 2 hrs
  6. customthen evaporated
  7. extractionextracted with ether (2×250 mL)
  8. washThe ether extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-65ab7ec7382945078d1216bd30267ee8
Source dataset
uspto-grants-2008_05
Patent number
US07371748B2

Reaction notes

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