Water → HCID 22253991, compound

HRID 1955053Notes

Reaction equation

HRID 1955053 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 dissolved in glacial acetic acid and stirred at room temperature. Bromine (2.5 equivalents) was added to the above mixture dropwise and stirring continued at room temperature for 4 hours. Water was added to the reaction mixture and the 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 ethyl acetate extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford a solid which was re-crystallized from 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. stirringstirring
  2. extractionthe mixture was then extracted with 2×25 ml ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate, and water
  4. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a solid which
  8. customwas re-crystallized from ethyl acetate/hexane 1:1 v/v

Sources & evidence

ORD record
ord-0280396477cf40bd9edefc9d241b2c5b
Source dataset
uspto-grants-2000_09
Patent number
US06124331

Reaction notes

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