Hydrogen Bromide → HCID 71063079, compound

HRID 1506788Notes

Reaction equation

HRID 1506788 reaction equation
Br.C[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9]([CH2:16][C:17]([O:19]CC)=[O:18])([CH3:15])[CH2:8][CH2:7]2>O>[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9]([CH2:16][C:17]([OH:19])=[O:18])([CH3:15])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 71062681HCID 71062681, compound

Product 1

HCID 71063079HCID 71063079, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous HBr (300 mL) was added to 3A (30 g, 109 mmol), and the reaction mixture was refluxed for 5 h. The reaction mixture was then brought to room temperature, diluted with water and extracted with ethyl acetate (2×300 mL). The separated organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 40% ethyl acetate in hexanes to afford the title compound (22 g, 73%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 12.08 (bs, 1H), 10.29 (s, 1H), 7.74 (d, J=8.4 Hz, 1H), 6.7 (m, 1H), 6.62 (m, 1H), 3.0-2.71 (m, 3H), 2.49-2.33 (m, 2H), 1.8 (m, 1H), 1.1 (s, 3H). ESI-MS m/z: 235 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. customwas then brought to room temperature
  3. extractionextracted with ethyl acetate (2×300 mL)
  4. dry with materialThe separated organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2147783b2df742d2867ac93b5cfb2497
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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