2-Bromoethanol → HCID 18787014, compound

HRID 1107273Notes

Reaction equation

HRID 1107273 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9](Cl)[CH2:10][C:4]=2[CH:3]=1.[Br:19][CH2:20][CH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:19][CH2:20][CH2:21][O:22][CH:9]1[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6][C:5]2[C:16]([Cl:18])=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=2[CH2:10]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 12654309HCID 12654309, compound

Product 1

HCID 18787014HCID 18787014, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2,4,10-trichloro-10,11-dihydrodibenzo[b,f]thiepine (2.5 g, 8.6 mmol, prepared as described in Coll. Czech. Chem. Commun. 46, 781, 1981), 2-bromoethanol (12.5 g, 100 mmol) and potassium carbonate (4.0 g, 30 mmol) in dichloromethane (20 ml) was stirred at 40° C. for 11 h. The solid was filtered off and the filtrate was evaporated in vacuo. The residue (3.4 g) was dissolved in a mixture of diethyl ether and light petroleum (1:1) (40 ml) and left to stand in a refrigerator for a week, affording after isolation 2.6 g (80%) of 10-(2-bromoethoxy)-2,4-dichloro-10,11-dihydrodibenzo[b,f]thiepine.

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue (3.4 g) was dissolved in a mixture of diethyl ether and light petroleum (1:1) (40 ml)
  4. waitleft
  5. waitto stand in a refrigerator for a week

Sources & evidence

ORD record
ord-00441cce74c84c3ab913362f3689fafc
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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