Boron tribromide → HCID 11677309, compound

HRID 1992907Notes

Reaction equation

HRID 1992907 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][C:33]([F:36])([F:35])[F:34])=[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:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:7]([CH2:31][CH2:32][C:33]([F:34])([F:35])[F:36])=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68536194HCID 68536194, compound

Product 1

HCID 11677309HCID 11677309, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl ether (128) (0.15 g, 0.31 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 97 mg (67%) of the title compound (129) as a light yellow solid. mp 118-120° C. 1H NMR (400 MHz, CH3OH-d4): δ 2.15-2.30 (m, 2H), 2.80-2.90 (m, 2H), 6.26 (d, J=15.9 Hz, 1H), 6.57 (d, J=8.6 Hz, 2H), 7.00 (dd, J1=9.0 Hz, J2=2.3 Hz, 1H), 7.16-7.20 (m, 3H), 7.22-7.32 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.59 (s, 1H), 7.62 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 479 (M+H)+, m/z 477 (M−H)−. Anal. Calc for C28H21F3O4.0.25H2O: C, 69.63; H, 4.49. Found: C, 69.63; H, 4.41.

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-bd52a013d8194e5787e7e03c5a6ec29f
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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