Water → 6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

HRID 61780

Reaction equation

HRID 61780 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C1C(=O)N([Br:23])C(=O)C1.O>CC#N>[Br:23][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[C:10]([CH3:13])([CH3:14])[C:9](=[O:15])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2×

Product 1

HCID 545785436-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 2.0 g, 9.791 mmol) was dissolved in CH3CN (40 mL), added with NBS (1.92 g, 1.1 eq.), and the mixture was stirred at room temperature for 2.5 hr. The reaction solution was added to water (40 mL), and the precipitated solid was filtered to obtain the title compound (white powder, 2.55 g, 92%).

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-8e9ae7628b6f4ada9bc74a2a53f2b1c7
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

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