HCID 71062618, compound → HCID 71063083, compound

HRID 1506784Notes

Reaction equation

HRID 1506784 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH2:19][C:20]([O:22]CC)=[O:21])([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:7][CH2:6]2>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH2:19][C:20]([OH:22])=[O:21])([CH2:14][C:15]([F:16])([F:17])[F:18])[CH2:7][CH2:6]2

Participants

3

Reactant 1

HCID 71062618HCID 71062618, compound

Product 1

HCID 71063083HCID 71063083, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Aqueous HBr (100 mL) was added to 1D (10 g, 29 mmol), and the reaction mixture was refluxed overnight. The reaction mixture was then brought to room temperature and extracted with ethyl acetate (2×100 mL). The organic layer was dried over sodium sulfate and filtered. The filtrate was removed under reduced pressure to afford crude compound (8 g) as a solid, which was carried on to the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 12.4 (s, 1H), 10.4 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 6.75 (dd, J1=2.4 Hz, J2=8.8 Hz, 1H), 6.64 (d, J=2.4 Hz, 1H), 3.0-2.85 (m, 3H), 2.73 (d, J=16.4 Hz, 1H), 2.7-2.61 (m, 1H), 2.48 (m, 1H), 2.38 (m, 1H), 2.11 (m, 1H). ESI-MS m/z: 301 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customwas then brought to room temperature
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-79e9dc02c6714540999b30e2f977c129
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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