1,1-Dichloroethane → 1-Bromo-4-cyclopropoxybenzene

HRID 646150Notes

Reaction equation

HRID 646150 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]=[CH2:10])=[CH:4][CH:3]=1.Cl[CH2:12]I.ClC(Cl)C.C([Zn]CC)C>[NH4+].[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:12][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 11644ChloroiodomethaneHCID 114013721-Bromo-4-(ethenyloxy)benzeneHCID 178418750HCID 178418750, compound

Product 1

HCID 509986941-Bromo-4-cyclopropoxybenzeneYield 94.7%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To mixture of 1-bromo-4-vinyloxybenzene (11.5 g, 58 mmol), chloroiodomethane (41 g, 232 mmol) and dichloroethane (180 mL) was added diethylzinc (15% solution in hexanes-95.5 mL, 116 mmol) over 3 h at 0° C. After 30 min stirring, NH4Cl solution (200 mL, aq. sat.) and light petrol (300 mL) was added. The organic phase was separated and concentrated in vacuo (8 bar, 50° C.). The residue was redissolved in light petrol and the insoluble material was filtered off. The filtrate was concentrated to afford sub-title compound (11.7 g, 94%).

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated in vacuo (8 bar, 50° C.)
  3. dissolutionThe residue was redissolved in light petrol
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e22e0e832fa649e7a2adf22246ab6cda
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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