Boron tribromide → HCID 11619024, compound

HRID 1992934Notes

Reaction equation

HRID 1992934 reaction equation
[CH2:1]([C:5]1[C:6]([C:27]2[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=2)=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:5]1[C:6]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 44580027HCID 44580027, compound

Product 1

HCID 11619024HCID 11619024, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (163) (0.12 g, 0.27 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 95 mg (82%) of the title compound (164) as a white solid. mp 107-109° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.78 (t, J=7.4 Hz, 3H), 1.15-1.29 (m, 2H), 1.40-1.50 (m, 2H), 2.62 (t, J=7.9 Hz, 2H), 6.26 (d, J=15.9 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 6.68 (d, J=8.4 Hz, 2H), 6.96 (d, J=8.6 Hz, 2H), 7.30-7.40 (m, 3H), 7.47 (t, J=7.9 Hz, 1H), 7.53 (d, J=15.9 Hz, 1H), 7.71 (s, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.88 (d, J=8.2 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+, m/z 437 (M−H)−. Anal. Calc for C29H26O4.⅙H2O: C, 78.89; H, 6.01. Found: C, 78.71; H, 5.91.

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-d87c3c6913c44598a9c7cd35ff8997e5
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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