1,3-Cyclohexanedione → 8-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

HRID 2179361Notes

Reaction equation

HRID 2179361 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]N)=[CH:5][CH:4]=1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1>>[Br:2][C:3]1[CH:8]=[CH:7][C:6]2[O:9][C:11]3[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]=3[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 67132126O-(4-bromophenyl)hydroxylamine hydrochloride

Product 1

HCID 681091618-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-oneYield 35%

Procedure

The product of Example 29, step A (1.0 g, 4.45 mmol) and cyclohexane-1,3-dione (750 mg, 6.68 mmol) were reacted following the procedure of Example 44, step A. Purification by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate) provided 8-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (410 mg, 35%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.20 (d, J=1.8 Hz, 1H), 7.42 (dd, J=8.7, 2.1 Hz, 1H), 7.33 (dd, J=8.7, 2.7 Hz, 1H), 3.04 (t, J=6.3 Hz, 2H), 2.61 (t, J=6.0 Hz, 2H), 2.28 (m, 2H).

Workup

  1. customPurification by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8b0b0cfec4f74d0091bc362149558590
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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