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

HRID 2202437Notes

Reaction equation

HRID 2202437 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 hours. The reaction solution was poured into 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-d48c647f742f42ee94d2c18a17220a40
Source dataset
uspto-grants-2016_06
Patent number
US09365514B2

Reaction notes

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