Boron tribromide → HCID 11561520, compound

HRID 1992900Notes

Reaction equation

HRID 1992900 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][CH2:33][CH2:34][CH3:35])=[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][CH2:33][CH2:34][CH3:35])=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68536346HCID 68536346, compound

Product 1

HCID 11561520HCID 11561520, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (116) (0.15 g, 0.32 mmol) was treated with BBr3 in CH2Cl2 to give the crude product as orange viscous oil, which was purified by reverse phase preparation HPLC on Agilent 1100 to afford 79 mg (54%) of the title compound (117) as a light yellow solid. mp 110-113° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.77 (t, J=6.8 Hz, 3H), 1.05-1.20 (m, 4H), 1.35-1.50 (m, 2H), 2.54 (t, J=7.8 Hz, 2H), 6.25 (d, J=16.0 Hz, 1H), 6.55 (d, J=8.8 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.2 Hz, 1H), 7.08-7.15 (m, 3H), 7.17-7.27 (m, 3H), 7.33 (d, J=8.8 Hz, 2H), 7.48-7.57 (m, 2H), 7.59 (d, J=9.2 Hz, 1H). LCMS (ESI): m/z 451 (M−H)−. Anal. Calc for C30H28O4.0.25H2O: C, 78.84; H, 6.29. Found: C, 78.80; H, 6.14.

Workup

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

Sources & evidence

ORD record
ord-b7acb7c7ed774c4eaf27b5a0e5b116ee
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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