Water → HCID 22253991, compound

HRID 325090Notes

Reaction equation

HRID 325090 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[Br:14]Br.O>C(O)(=O)C>[Br:14][CH:8]1[C:7](=[O:12])[C:6]2[CH:13]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[S:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 14892863HCID 14892863, compound

Product 1

HCID 22253991HCID 22253991, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Fluoro-2,3,4,5-tetrahydro-1-benzothiepin-5-one (1 equivalent) was also dissolved in glacial acetic acid and stirring continued at room temperature. Bromine (2.5 equivalents) was added dropwise and stirring continued at room temperature for 4 hours. Water was added to the reaction mixture was then extracted with 2×25 ml ethyl acetate. The combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate, and water. The combined extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a solid which was recrystallized from the ethyl acetate/hexane 1:1 v/v to afford 4-bromo-7-fluoro-2,3,4,5-tetrahydro-1-benzothiepin-5-one: 1H NMR (CDCl3) δ 7.55 (dd, 1H, J=2.7, 9.0 Hz), 7.44 (dd, 1H, J=8.7, 5.1 Hz), 7.11 (Apparent dt, 1H, J=2.7, 4.8 Hz), 5.34 (dd, 1H, J=5.7, 10.2 Hz), 3.20-2.50 (m, 4H).

Workup

  1. customcontinued at room temperature
  2. stirringstirring
  3. extractionwas then extracted with 2×25 ml ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate, and water
  5. extractionThe combined extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a solid which
  10. customwas recrystallized from the ethyl acetate/hexane 1:1 v/v

Sources & evidence

ORD record
ord-af65f5c69efe4e83b31790108b37d0b0
Source dataset
uspto-grants-2001_04
Patent number
US06222040B1

Reaction notes

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