Water → HCID 18787011, compound

HRID 1107269Notes

Reaction equation

HRID 1107269 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]([OH:11])[CH2:10][C:4]=2[CH:3]=1.[Br:18][CH2:19][CH2:20]O.B(F)(F)F.CCOCC.O>C1C=CC=CC=1>[Br:18][CH2:19][CH2:20][O:11][CH:9]1[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6][C:5]2[CH:16]=[CH:17][C:2]([CH3:1])=[CH:3][C:4]=2[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 108982-BromoethanolHCID 11834917HCID 11834917, compound

Product 1

HCID 18787011HCID 18787011, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

To a solution of 2-methyl-10,11-dihydrodibenzo[b,f]thiepin-10-ol (3.63 g, 15 mmol, prepared as described in Ger. Offen. 2,336,130, 1974) and 2-bromoethanol (2.5 g, 20 mmol) in absolute benzene (25 ml), a solution of boron trifluoride etherate (2.25 g. 15.8 mmol) in absolute benzene (10 ml) was dropwise added at 10-15° C. over 15 minutes. The reaction mixture was stirred at 10-15° C. for 2 h and water (18 ml) was added. The organic layer was separated, washed with water (2×25 ml), dried (Na2SO4) and evaporated in vacuo to give 3.83 g (73%) crude 10-(2-bromoethoxy)-2-methyl-10,11-dihydrodibenzo[b,f]thiepine, which was used without further purification in the next step.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×25 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2811e8ac7040432cafb4fc7e0e083c62
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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