Iodine → HCID 13193691, compound

HRID 231132Notes

Reaction equation

HRID 231132 reaction equation
II.Br[C:4]1[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1.[CH3:21][C:22](Cl)=[O:23].[NH4+].[Cl-]>C1COCC1>[CH2:10]1[O:9][C:8]2[C:7](=[CH:6][C:5]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]([C:22](=[O:23])[CH3:21])[CH:12]=2)[O:11]1

Participants

6

Reactant 4

HCID 807IodineHCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 14501061HCID 14501061, compound

Product 1

HCID 13193691HCID 13193691, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In a flame-dried flask was added under argon Mg (0.58 g, 0.024 mol), a few crystals of I2 and dry THF (10 ml). A solution of 6-bromo-5-(phenylmethoxy)-1,3-benzodioxole (6.14 g, 0.02 mol) in dry THF (15 ml) was added dropwise under reflux. Heating was continued for 3 hours. The Grignard reagent was added over 1.5 h to a solution of freshly distilled CH3COCl (7 ml) in dry THF (20 ml) held at -78° C. The stirred reaction mixture was allowed to warm to room temperature overnight, poured into 2N-NH4Cl (100 ml) solution and extracted with chloroform (3×50 ml). The organic layer was washed with 10% NaOH and brine, and dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to flash chromatography (silica gel) using petroleum ether--CHCl3 (2:1) as eluent affording 3.87 g (71.6%) of 1-[4,5-(methylenedioxy)-2-(phenylmethoxy)phenyl]ethanone mp (EtOH) 116.5°-117° C.; IR(KBr) 1652 (carbonyl) cm-1 ; NMR (CDCl3, 90 MHz) δ 2.55 (S, 3H, CH3), 5.11 (S, 2H, CH2Ph), 5.98 (S, 2H, OCH2O), 6.58 (S, 1H, ArH), 7.34 (S, 1H, ArH), 7.40 (S, 5H, CH2Ph). Anal. calcd. for C16H14O4 : C, 71.10; H, 5.22. Found: C, 70.96; H, 5.29.

Workup

  1. additionIn a flame-dried flask was added under argon Mg (0.58 g, 0.024 mol)
  2. temperatureunder reflux
  3. temperatureHeating
  4. customheld at -78° C
  5. customThe stirred reaction mixture
  6. extractionextracted with chloroform (3×50 ml)
  7. washThe organic layer was washed with 10% NaOH and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf89ece7368a4cdcb1406d51c177d0a3
Source dataset
uspto-grants-1989_07
Patent number
US04845121

Reaction notes

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