Boron tribromide → HCID 25030037, compound

HRID 2280585Notes

Reaction equation

HRID 2280585 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.B(Br)(Br)Br>C(Cl)Cl.CO>[OH:2][C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 25029795HCID 25029795, compound

Product 1

HCID 25030037HCID 25030037, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ketone 17 was dissolved in dry DCM and the resulting solution was cooled to −78° C. BBr3 (1.5 eq, 0.49 mM) was then added drop wise and the reaction mixture was allowed to warm to room temperature and was stirred for an additional 12 hours. After the completion of the reaction as determined by TLC, the reaction mixture was diluted with methanol, and then washed with bicrab, water brine. The product was then subjected to column chromatography using 20% EtOAc/hexanes as the solvent system. Yield=46.5% (Rf=0.31; 20% EtOAc/Hexanes) 1H NMR, 300 MHz Varian, CDCl3 δ 7.88 (d, J=8.4 Hz, 2H), 7.59 (t, J=7.2 Hz, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.47 (m, 2H), 7.43 (d, J=6.3 Hz, 2H), 7.38 (s, 1H), 7.34 (s 7.27 (m, 1H), 2.46 (s, 3H), MS: m/z (ESI, pos.)=325.5 ([M+23]). HPLC retention time: 11.246 min. and 10.804 min; purity 97.92%.

Workup

  1. temperatureto warm to room temperature
  2. customAfter the completion of the reaction
  3. washwashed with bicrab, water brine
  4. customHPLC retention time: 11.246 min. and 10.804 min

Sources & evidence

ORD record
ord-ef71ed764d3c4621b889afa96496b64f
Source dataset
uspto-grants-2015_09
Patent number
US09139546B2

Reaction notes

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