Boron tribromide → HCID 11583055, compound

HRID 1992915Notes

Reaction equation

HRID 1992915 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:30][CH2:31][CH3:32])[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:9]2[O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:33]C.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:30][CH2:31][CH3:32])[C:8]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:9]2[O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[OH:33]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68536417HCID 68536417, compound

Product 1

HCID 11583055HCID 11583055, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (140) (0.15 g, 0.33 mmol) was treated with BBr3 in CH2Cl2 to give the crude product as a brown viscous oil, which was purified by reverse phase preparation HPLC on Agilent 1100 to afford 122 mg (84%) of the title compound (141) as a light yellow solid. mp 118-120° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.77 (t, J=7.3 Hz, 3H), 1.40-1.55 (m, 2H), 2.52 (t, J=7.6 Hz, 2H), 6.27 (d, J=15.9 Hz, 1H), 6.55 (d, J=8.4 Hz, 2H), 7.08-7.16 (m, 2H), 7.20-7.40 (m, 7H), 7.48-7.56 (m, 2H). LCMS (APCI): m/z 443 (M+H)+, m/z 441 (M−H)−. Anal. Calc for C29H25FO4.0.4H2O: C, 74.79; H, 5.33. Found: C, 74.71; H, 5.21.

Workup

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

Sources & evidence

ORD record
ord-d3604641c4bb4ed785de954f257ccc94
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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