1,3-Dibromobenzene → HCID 58345149, compound

HRID 1888012Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.Cl.[NH:10]1[CH2:13][CH2:12][CH2:11]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[Na]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:4]1[CH:3]=[C:2]([N:10]2[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1,3-dibromobenzene (472 mg, 2 mmol) in toluene (5 mL), were added azetidine hydrochloride (187 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), racemic BINAP (93 mg, 0.15 mmol) and sodium tert-butoxyde (230 mg, 2.4 mmol). The reaction was heated to 80° C. for 12 hr under nitrogen gas. The reaction mixture was filtered through celite and the filtered mixture was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate: methanol=10:0:0 to 9:1:0.1) gave the product (51 mg, 12%). 400 M Hz 1H-NMR (CDCl3) δ: 7.04 (t, J=8.0 Hz, 1H), 6.82 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.55 (t, J=2.0 Hz, 1H), 6.33 (dd, J=7.7 Hz and 2.0 Hz, 1H), 3.87 (t, J=7.2 Hz, 4H), 2.40-2.34 (m, 2H); LCMS: 212[M+H].

Workup

filtrationThe reaction mixture was filtered through celite
customthe filtered mixture was evaporated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate: methanol=10:0:0 to 9:1:0.1)

Sources & evidence

ORD record: ord-10e5e235a61e4c82a5daedb61f810722
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501770B2

Reaction notes

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