Diethyl Ether → Tert-butyl 2-(4-chloro-3-isopropoxyphenyl)acetate

HRID 1773968Notes

Reaction equation

HRID 1773968 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([O:9][CH:10]([CH3:12])[CH3:11])[CH:3]=1.[Cl-].[C:14]([O:18][C:19](=[O:22])[CH2:20][Zn+])([CH3:17])([CH3:16])[CH3:15].CCOCC>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:14]([O:18][C:19](=[O:22])[CH2:20][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([O:9][CH:10]([CH3:12])[CH3:11])[CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 210710294-Bromo-1-chloro-2-isopropoxybenzeneHCID 178451183HCID 178451183, compound

Product 1

HCID 89648442Tert-butyl 2-(4-chloro-3-isopropoxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-bromo-1-chloro-2-isopropoxy-benzene (2.48 g, 9.8 mmol, 1.0 eq.) and bis(tri-tert-butylphosphine)palladium(0) (501 mg, 0.98 mmol, 0.1 eq.) in dioxane (84 mL), a 0.5M solution of 2-tert-butoxy-2-oxoethylzinc chloride in Et2O (35.3 mL, 17.6 mmol, 1.8 eq.) was added. The resulting mixture was stirred at r.t. for 2 days. The mixture was filtered over celite and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+8% AcOEt) to yield the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered over celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+8% AcOEt)

Sources & evidence

ORD record
ord-4f3d20a669414950bc9d986e848ce8f1
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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