Potassium Phosphate, Tribasic → 1-Bromo-4-chloro-2-cyclopropylbenzene

HRID 1504517Notes

Reaction equation

HRID 1504517 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1I.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH:1]1[CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 510000721-Bromo-4-chloro-2-iodobenzene

Product 1

HCID 665211071-Bromo-4-chloro-2-cyclopropylbenzene

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of cyclopropylboronic acid (2.104 g, 24.49 mmol), 1-bromo-4-chloro-2-iodobenzene (5.700 g, 17.96 mmol), potassium phosphate (13.86 g, 65.3 mmol), and PdCl2(dppf)-DCM adduct (0.667 g, 0.816 mmol) in 18 mL dioxane and 6 mL water was heated to 100° C. overnight. The reaction mixture was then diluted with DCM and washed with water. The organics were dried over MgSO4 and concentrated. The crude residue was used in the next step without purification. m/z (ESI) does not ionize in H+ mode.

Workup

  1. washwashed with water
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-a2a283699b80480bbf7d6db40a624a51
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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