Boron tribromide → HCID 11495320, compound

HRID 1992832Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 26 (122 mg, 0.29 mmol, 1 equiv) was dissolved in CH2Cl2 (25 mL) and cooled to 0° C. under N2. BBr3 (135 μL, 1.42 mmol, 5 equiv) was added dropwise and the resulting solution was allowed to stir at 0° C. for 3 h. The reaction mixture was then poured into ice and the product extracted into EtOAc (250 mL). The organics were washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chromatography (50% EtOAc in hexanes) to provide the title compound (27) (122 mg, 66%) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): δ 9.89 (s, 1H), 7.61-7.51 (m, 3H), 7.39 (m, 1H), 7.31-7.15 (m, 7H), 7.01 (m, 1H), 6.38 (m, 2H), 2.15 (s, 3H). MS m/z 413.4 (M−H)−.

Workup

additionThe reaction mixture was then poured into ice
extractionthe product extracted into EtOAc (250 mL)
washThe organics were washed with saturated aqueous NaCl (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by silica gel flash column chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6bc44ee056b64d9080409d85d42e3309
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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