Water → HCID 22000390, compound

HRID 917510Notes

Reaction equation

HRID 917510 reaction equation
[CH2:1]1[CH2:8][C:7]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:6]=2[C:4](=[O:5])[CH2:3][CH2:2]1.[Br:14]Br.O>C(O)(=O)C>[Br:14][CH:3]1[CH2:2][CH2:1][CH2:8][C:7]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:6]=2[C:4]1=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 5790508-Fluoro-1-benzosuberone

Product 1

HCID 22000390HCID 22000390, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 8-fluoro-1-benzosuberone (20.00 g, 112.2 mmol) in glacial acetic acid (125 ml) was added bromine (5.8 ml, 112.6 mmol) dropwise. Once the addition was complete, the solution was poured into water (400 ml) and extracted with EtOAc (500 ml). The extract was separated and washed with water (500 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield 100% (28.9 g) of the desired product as a viscous oil: 1H-NMR (CDCl3) δ 2.00 (2H, m), 2.33 (2H, m), 2.84 (1H, m), 3.00 (1H, m), 4.83 (1H, m), 7.13 (2H, m), 7.29 (1H, dd).

Workup

  1. additionOnce the addition
  2. extractionextracted with EtOAc (500 ml)
  3. customThe extract was separated
  4. washwashed with water (500 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-030aaf813e244a9bb959f1a40cf3426d
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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