Triphenylphosphine → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

HRID 391408

Reaction equation

O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile (0.33 mg, 1.64 mmol) and triphenylphosphine (0.86 g, 3.28 mmol) were combined in methylene chloride (6 mL) and cooled to 0° C. N-Bromosuccinimide (0.61 mg, 3.43 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with methylene chloride, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.36 g (83%). 1H-NMR (CDCl3, 500 MHz) δ 7.97 (s, 2H), 7.84 (s, 1H), 4.50 (s, 2H).

Workup

temperatureto warm to room temperature
washwashed with concentrated sodium bicarbonate (2×), brine (2×)
dry with materialdried over sodium sulfate
concentrationconcentrated
customColumn chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.36 g (83%)

Sources & evidence

ORD record: ord-7e23b24fbf744967ae3683bf41d8c9a8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383821B2

Linked notes

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