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Sulfuric Acid → 10-Benzo[1,3]dioxol-5-yl-5-bromo-9H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-one

HRID 2354607
Notes
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Reaction equation

HRID 2354607 reaction equation
[Br:1]N1C(=O)CCC1=O.OS(O)(=O)=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:39])[C:25]=4[CH:26]=[C:27]4[C:35]=3[C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=[CH:28]4)=[CH:22][C:17]=2[O:16][CH2:15]1>C1COCC1.CCOC(C)=O>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[C:24]4[CH2:38][O:37][C:36](=[O:39])[C:25]=4[CH:26]=[C:27]4[C:35]=3[C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=[C:28]4[Br:1])=[CH:22][C:17]=2[O:16][CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 177023Helioxanthin

Product 1

HCID 527381110-Benzo[1,3]dioxol-5-yl-5-bromo-9H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-oneYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

N-bromosuccinimide (10.7 mg, 0.06 mmol) and concentrated H2SO4 (5 μL) were added to a solution of 2 (15.4 mg, 0.044 mmol) in THF (1 mL). The solution was stirred at room temperature for 20 h, and then diluted with EtOAc (30 μL). The same workup and purification procedure as described for the isolation of 37 gave 38 (12 mg, 64%) as a pale yellow powder. mp 256° C. (decomp.); 1H NMR (CDCl3) δ 8.89 (s, 1H, H4), 7.65 (s, 1H, H6), 6.76-6.91 (m, 3H, H2′+H5′+H6′), 6.08 (AB, 2H, 3′,4′-OCH2O—, Δδ=8.7 Hz, J=1.5 Hz), 5.97 (AB, 2H, 7,8-OCH2O—, Δδ=7.8 Hz, J=1.5 Hz), 5.22 (q, 2H, lactone-CH2—, J=8.4 Hz); MS (EI) m/z 428 [M+2]+, 426 [M]+.

Workup

  1. customThe same workup and purification procedure

Sources & evidence

ORD record
ord-e36a056edac54798ba6368aabe3e0907
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07754718B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes