Boron tribromide → HCID 11633183, compound

HRID 1992927Notes

Reaction equation

HRID 1992927 reaction equation
[CH:1]1([C:4]2[C:5]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:6]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=3)[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:14]C)=[CH:9][CH:8]=3)[CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:4]2[C:5]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:6]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=3)[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([OH:14])=[CH:9][CH:8]=3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68539395HCID 68539395, compound

Product 1

HCID 11633183HCID 11633183, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (155) (0.14 g, 0.32 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 69 mg (51%) of the title compound (156) as an off-white solid. mp 242-243° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.75-0.85 (m, 4H), 1.60-1.70 (m, 1H), 6.26 (d, J=15.9 Hz, 1H), 6.57 (d, J=8.6 Hz, 2H), 7.02 (dd, J1=9.0 Hz, J2=2.0 Hz, 1H), 7.12 (d, J=1.9 Hz, 1H), 7.16-7.28 (m, 6H), 7.34 (d, J=8.6 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.58 (d, J=9.0 Hz, 1H). LCMS (APCI): m/z 423 (M+H)+, m/z 421 (M−H)−. Anal. Calc for C28H22O4.1.25H2O: C, 75.58; H, 5.55. Found: C, 75.34; H, 5.34.

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-d891d27a93fb47debbdf0c194c3c6e10
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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