Boron tribromide → HCID 11517461, compound

HRID 1992886Notes

Reaction equation

HRID 1992886 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:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=1)=[C:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:7]([CH2:31][CH2:32][CH3:33])=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[CH:18][CH:19]=1)=[C:8]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:7]([CH2:31][CH2:32][CH3:33])=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68537461HCID 68537461, compound

Product 1

HCID 11517461HCID 11517461, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (100) (0.15 g, 0.34 mmol) was treated with BBr3 in CH2Cl2 to give the crude product as a yellow viscous oil, which was purified by reverse phase preparation HPLC on Agilent 1100 to afford 96 mg (66%) of the title compound (101) as pale yellow solid. mp 120-122° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.77 (t, J=7.4 Hz, 3H), 1.45-1.55 (m, 2H), 2.52 (t, J=7.8 Hz, 2H), 6.25 (d, J=15.9 Hz, 1H), 6.55 (d, J=8.7 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 3H), 7.18-7.27 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.48-7.56 (m, 2H), 7.69 (d, J=9.0 Hz, 1H). LCMS (ESI): m/z 425 (M+H)+, m/z 423 (M−H)−. Anal. Calc for C28H24O4.0.33H2O: C, 78.12; H, 5.78. Found: C, 77.97; H, 5.58.

Workup

  1. customto give the crude product as a yellow viscous oil, which
  2. customwas purified by reverse phase preparation HPLC on Agilent 1100

Sources & evidence

ORD record
ord-8d5634bd14ff4eea8cf607387278e635
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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