Bromine → Methyl 3-(2-bromo-2-cyclopropylacetyl)-4-methylbenzoate

HRID 1487831Notes

Reaction equation

HRID 1487831 reaction equation
[CH:1]1([CH2:4][C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[CH3:17])[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:3][CH2:2]1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][CH:4]([CH:1]1[CH2:3][CH2:2]1)[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12][CH3:13])=[O:11])=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 90021671Methyl 3-(2-cyclopropylacetyl)-4-methylbenzoate2×

Product 1

HCID 90021300Methyl 3-(2-bromo-2-cyclopropylacetyl)-4-methylbenzoateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into a 100-mL round-bottom flask, was placed a solution of methyl 3-(2-cyclopropylacetyl)-4-methylbenzoate (compound 4.5, 150 mg, 0.65 mmol) in chloroform (15 mL). Bromine (40 μL, 0.78 mmol) in chloroform (2 mL) was added drop-wise to the reaction mixture. The resulting solution was stirred for 2 h at room temperature, then concentrated under reduced pressure to yield the title compound as a yellow oil (200 mg, crude), which was used in the next step without further purification.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a92c120a0f4b4003a384bec4706516bd
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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