(6-Iodo-2H-1,3-benzodioxol-5-yl)methanol → 6-iodobenzo[d][1,3]dioxole-5-carbaldehyde

HRID 1476720Notes

Reaction equation

HRID 1476720 reaction equation
[I:1][C:2]1[C:3]([CH2:11][OH:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[I:1][C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 323453(6-Iodo-2H-1,3-benzodioxol-5-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 108500326-iodobenzo[d][1,3]dioxole-5-carbaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(6-Iodobenzo[d][1,3]dioxol-5-yl)methanol (2.7 g, 9.7 mmol) in dry CH2Cl2 was added dropwise to PCC (3.1 g, 14.6 mmol) in dry CH2Cl2 at 0° C. under N2 atmosphere. The mixture was stirred at room temperature for 20 h. After reaction, the crude product was purified by column chromatography on silica gel (petroleum ether) to obtain 6-iodobenzo[d][1,3]dioxole-5-carbaldehyde (2 g, 77%) as white solid. LCMS: 277[M+1]+; 1H NMR (DMSO-d6) δ 6.20 (s, 2H), 7.28 (s, 1H), 7.61 (s, 1H), 9.79 (s, 1H).

Workup

  1. customAfter reaction
  2. customthe crude product was purified by column chromatography on silica gel (petroleum ether)

Sources & evidence

ORD record
ord-612f92f895c345358aa006852407f27c
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

Loading…