Iodine → (6-Iodo-2H-1,3-benzodioxol-5-yl)methanol

HRID 1476719Notes

Reaction equation

HRID 1476719 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=2[O:2]1.[I:12]I>C(Cl)(Cl)Cl>[I:12][C:8]1[C:5]([CH2:6][OH:7])=[CH:4][C:3]2[O:2][CH2:1][O:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 807IodineHCID 10322Piperonyl alcohol

Product 1

HCID 323453(6-Iodo-2H-1,3-benzodioxol-5-yl)methanolYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 3,4-(methylenedioxy)benzyl alcohol (1.8 g, 12 mmol) and CF3COOAg (3.434 g, 15.5 mmol) in dry CHCl3 (55 mL) at −5° C. was added I2 (3.9 g, 15.5 mmol) in portion. The resulting yellow mixture was maintain at −5° C. for 5 min, then filtered. The filtrate was washed with 20% Na2S2O3, dried and evaporated. The crude was purified by column chromatography on silica gel (petroleum ether) to obtain (6-iodobenzo[d][1,3]dioxol-5-yl)methanol (1.8 g, 56%) as a white solid. LCMS: 279[M+1]+; 1H NMR (DMSO-d6) δ 4.31 (d, 2H, J=4.2 Hz), 5.40 (t, 1H, J=4.2 Hz), 6.03 (s, 2H), 7.03 (s, 1H), 7.34 (s, 2H).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 20% Na2S2O3
  3. customdried
  4. customevaporated
  5. customThe crude was purified by column chromatography on silica gel (petroleum ether)

Sources & evidence

ORD record
ord-e494f6738b9e4660aa2deb545f788bb1
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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