2,4-Dichlorobenzaldehyde → 1,3-Benzodioxole-4-carboxaldehyde

HRID 131167

Reaction equation

HRID 131167 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10](=[O:13])CBr)[C:4]=2[O:3][CH2:2]1.ClC1C=C(Cl)C=CC=1C=O>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]=[O:13])[C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 134042,4-DichlorobenzaldehydeHCID 218649771-Benzo[1,3]dioxol-4-yl-2-bromo-ethanone

Product 1

HCID 822641,3-Benzodioxole-4-carboxaldehyde

Procedure

This compound was prepared using 1-Benzo[1,3]dioxol4-yl-2-bromo-ethanone prepared in method I-7 (0.15 g, 10.62 mmol), in the manner described for 3-amino-5,6,7,8-tetrahydro-naphtho[2,3-b]furan-2-yl)-(2,4-dichloro-phenyl)-methanone (Method III-1):, affording 0.36 g (21%) of 3-Amino-5,6,7,8-tetrahydro-naphtho-[2,3-b]furan-2-yl)benzo[1,3]dioxol-4-yl-methanone as a yellow solid. 1H-NMR (MeOH-d4) δ 7.40 (s, 1H), 7.31 (dd, J=8 Hz, 1 Hz), 6.97 (dd, J=7 Hz, 1 Hz, 1 H), 6.82 (s, 1H), 6.19 (s, 2H), 2.68-2.60 (m, 4H), 1.68-1.62 (m, 4H); MS LC-MS (MH+=336.2), RT=3.86 min.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b877ff6c0b39487d9fce633ae828f388
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Linked notes

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