Bromine → 2-Bromo-1-(6-bromonaphthalen-2-yl)ethanone

HRID 1471164Notes

Reaction equation

HRID 1471164 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14](=[O:16])[CH3:15])[CH:8]=[CH:7]2>C(Cl)Cl>[Br:1][CH2:15][C:14]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([Br:3])[CH:5]=2)[CH:10]=1)=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 124330821-(6-Bromonaphthalen-2-yl)ethanone

Product 1

HCID 126988982-Bromo-1-(6-bromonaphthalen-2-yl)ethanoneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.682 mL, 13.3 mmol) in DCM (20 mL) was added to a solution of 1-(6-bromonaphthalen-2-yl)ethanone (3.30 g, 13.3 mmol) (>90% purity) in DCM (60 mL) and the reaction was stirred at rt overnight. The reaction mixture was concentrated to yield 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (4.35 g) as an off white solid which was used without further purification. LC-MS retention time 2.177 min; m/z 342.92 (MNa+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 10u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (400 MHz, chloroform-d) δ ppm 8.49 (s, 1 H), 8.03-8.10 (m, 2 H), 7.86 (d, J=8.5 Hz, 1 H), 7.85 (d, J=8.8 Hz, 1 H), 7.67 (dd, J=8.8, 2.0 Hz, 1 H), 4.56 (s, 2 H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7820028f632849debd87531c10d10db0
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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