Boron tribromide → HCID 11524670, compound

HRID 1992869Notes

Reaction equation

HRID 1992869 reaction equation
[CH3:1][CH:2]([C:4]1[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14]C)=[CH:9][CH:8]=2)[CH3:3].B(Br)(Br)Br>C(Cl)Cl>[OH:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6]([O:16][C:17]1[CH:18]=[CH:19][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=1)=[C:5]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:4]([CH:2]([CH3:3])[CH3:1])=[CH:13]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68537308HCID 68537308, compound

Product 1

HCID 11524670HCID 11524670, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The methyl ether (75) (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 102 mg (70%) of the title compound (76) as a light yellow solid. mp 198-199° C. 1H NMR (400 MHz, CH3OH-d4): δ 1.18 (d, J=6.8 Hz, 6H), 2.88 (sept, J=6.8 Hz, 1H), 6.26 (d, J=15.9 Hz, 1H), 6.54 (d, J=8.6 Hz, 2H), 6.96 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.08-7.15 (m, 2H), 7.17 (d, J=2.2 Hz, 1H), 7.18-7.30 (m, 3H), 7.33 (d, J=8.6 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.56-7.64 (m, 2H). LCMS (ESI): m/z 425 (M+H)+, m/z 423 (M−H)−. HRMS (EI) Calc for C28H24O4: 425.1753 (M+•). Found: 425.1742.

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-938add16ec6741adbaa004ee98174e7d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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