Carbon tetrabromide → 4-(5-Bromopentyl)-1,1'-biphenyl

HRID 84347

Reaction equation

[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[1,1′-biphenyl]-4-pentanol (3.34 g, 13.90 mmol) and carbon tetrabromide (5.99 g, 18.07 mmol) were dissolved in dry methylene chloride (20 mL) and cooled to 0° C. Triphenyl phosphine (4.98 g, 18.07 mmol) in methylene chloride (10 mL) was added dropwise, and the mixture was stirred for 1 h at 0° C. The mixture was poured into hexanes (100 mL) and then filtered through a short silica gel column, washed with ethylacetate/hexanes (1/4). The combined organic solvents were evaporated to dryness under reduced pressure. The resulting residue was purified by column chromatography (hexanes:ethylacetate 30:1) to afford 4.18 g of the title compound. Yield: 99%. 1H NMR (300 MHz, CDCl3) δ 1.52 (m, 2H), 1.67 (m, 2H), 1.91 (m, 2H), 2.67 (t, J=7.5 Hz, 2H), 3.41 (t, J=6.9 Hz, 2H), 7.21-7.60 (m, 9H) ppm; 13C NMR (75 MHz, CDCl3) δ 28.2, 30.9, 33.0, 34.1, 35.6, 127.1, 127.2, 128.8, 128.9, 138.8, 141.2, 141.5 ppm.

Workup

filtrationfiltered through a short silica gel column
washwashed with ethylacetate/hexanes (1/4)
customThe combined organic solvents were evaporated to dryness under reduced pressure
customThe resulting residue was purified by column chromatography (hexanes:ethylacetate 30:1)

Sources & evidence

ORD record: ord-75c4efd9f15c4b379e8134645282c882
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846937B2

Linked notes

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