Boron tribromide → HCID 11719093, compound

HRID 1992876Notes

Reaction equation

HRID 1992876 reaction equation
[CH2:1]([C:5]1[C:6]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]C)=[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:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68536111HCID 68536111, compound

Product 1

HCID 11719093HCID 11719093, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether 84 (0.15 g, 0.33 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 (65%) of the title compound (85) as pale yellow solid. mp 128-130° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.74 (t, J=7.3 Hz, 3H), 1.10-1.25 (m, 2H), 1.35-1.45 (m, 2H), 2.50-2.60 (m, 2H), 6.25 (d, J=16.1 Hz, 1H), 6.55 (d, J=8.6 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.0 Hz, 1H), 7.08-7.18 (m, 3H), 7.18-7.28 (m, 3H), 7.33 (d, J=8.6 Hz, 2H), 7.46-7.58 (m, 2H), 7.59 (d, J=9.0 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+, m/z 437 (M−H)−. Anal. Calc for C29H26O4.0.4H2O: C, 78.15; H, 6.06. Found: C, 78.03; H, 6.00.

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-aeb52b09d1de4b6089d7b92b54fcc5fa
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…