2-Bromoethanol → HCID 18787012, compound

HRID 1107267Notes

Reaction equation

HRID 1107267 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH2:3]1.[Br:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:17][CH2:18][CH2:19][O:20][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1295732310-Chloro-10,11-dihydrodibenzo[b,f]thiepine

Product 1

HCID 18787012HCID 18787012, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

10-Chloro-10,11-dihydrodibenzo[b,f]thiepine (10 g, 0.041 mol, prepared as described in Monatshefte 96, 182, 1965) was slowly added to a mixture of 2-bromoethanol (44 g, 0.35 mol) and powdered potassium carbonate (10 g, 0.072 mol) at room temperature. After stirring for 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. The 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 was evaporated to give 13.8 g of crude 10-(2-bromoethoxy)-10,11-dihydrodibenzo[b,f]thiepine as an oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customThe dichloromethane 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 was evaporated

Sources & evidence

ORD record
ord-5129b10240d347ffbd20dd7e092f2c32
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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