Bromine → HCID 90438018, compound

HRID 589029Notes

Reaction equation

HRID 589029 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:5])[CH3:4]>C(Cl)(Cl)Cl.CCOC(C)=O>[Br:1][CH2:4][C:3]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:5]

Participants

5

Reactant 2

HCID 24408BromineHCID 13446028(4-(Azetidine-1-carbonyl)phenyl)boronic acid

Product 1

HCID 90438018HCID 90438018, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Bromine (1.2 g, 7.2 mmol) in chloroform (5 mL) was added drop wise to a solution of methyl (2-acetylphenoxy)acetate (1.5 g, 7.2 mmol) in chloroform (45 mL) at room temperature. The reaction mixture was stirred for 1 h at room temperature, diluted with EtOAc and washed with sodium bicarbonate water, brine, dried over magnesium sulfate and concentrated to give the sub-title compound as an oil which solidified (2.1 g, 100%). LCMS calc. for C11H12BrO4 (M+H)+: m/z=287.0, 289.0. found: 287.0, 289.0.

Workup

  1. washwashed with sodium bicarbonate water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-47e2872072bb4e50b6ec767e290005e2
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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