2-Bromoethanol → HCID 13295989, compound

HRID 1107270Notes

Reaction equation

HRID 1107270 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][CH:7](Cl)[C:6]=2[CH:17]=1.[Br:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][CH:7]([O:21][CH2:20][CH2:19][Br:18])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 12235706HCID 12235706, compound

Product 1

HCID 13295989HCID 13295989, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

8, 10-Dichloro-10,11-dihydrodibenzo[b,f]thiepine (10 g, 35.6 mmol, prepared as described in Coll. Czech. Chem. Commun. 33,183, 1968) was slowly added to a mixture of 2-bromoethanol (44 g, 0.352 mol) and powdered potassium carbonate (10 g, 0.072 mol) at 20° C. under stirring. After 6 h, dichloromethane (15 ml) was added and the reaction mixture was heated at 50° C. for 3 h. After cooling, dichloromethane (35 ml) was added and the mixture was filtered. Dichloromethane was evaporated and excess of 2-bromoethanol was distilled off in vacuo. The oily residue was dissolved in benzene (100 ml), washed with water (3×70 ml), dried (K2CO3) and the solvent evaporated to give 13.0 g of crude 8-chloro-10-(2-bromoethoxy)-10,11-dihydrodibenzo[b,f]thiepine as an oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customDichloromethane was evaporated and excess of 2-bromoethanol
  4. distillationwas distilled off in vacuo
  5. dissolutionThe oily residue was dissolved in benzene (100 ml)
  6. washwashed with water (3×70 ml)
  7. dry with materialdried (K2CO3)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-aa25e9082bf04dba8ebd96a3fc0bfc13
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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