2-Bromoethanol → 12-(2-bromo-ethoxy)-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene

HRID 323591Notes

Reaction equation

HRID 323591 reaction equation
Br[CH:2]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][O:5][C:4]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:3]1=2.[Br:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:20][CH2:21][CH2:22][O:23][CH:2]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][O:5][C:4]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:3]1=2

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2272777812-bromo-2,10-dichloro-12H-5,7-dioxadibenzo[a,d]cyclooctene

Product 1

HCID 2272788012-(2-bromo-ethoxy)-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cycloocteneYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 12-bromo-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene (900 mg, 2.5 mmol), 2-bromoethanol (3.75 g, 30 mmol) and potassium carbonate (1.0 g, 7.2 mmol) in dichloromethane (10 mL) was heated at 120° C. for 4 h. The reaction mixture was concentrated in vacuo, added water (25 mL) and the product extracted with ethyl acetate (3×25 mL). The combined organic phases were dried (MgSO4), filtered and evaporated to give 832 mg (82%) of 12-(2-bromo-ethoxy)-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionadded water (25 mL)
  3. extractionthe product extracted with ethyl acetate (3×25 mL)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-99ba4ba9db934e39a62f1dcf95d7d77a
Source dataset
uspto-grants-2001_04
Patent number
US06214820B1

Reaction notes

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