Pyridine → 4-(Bromomethyl)-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl

HRID 404325Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH3:22][C:23]1([CH3:45])[C:27]([C:28]2[CH:33]=[C:32]([CH2:34]O)[CH:31]=[CH:30][C:29]=2[C:36]2[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=2[F:44])=[CH:26][CH2:25][CH2:24]1.N1C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:34][C:32]1[CH:31]=[CH:30][C:29]([C:36]2[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=2[F:44])=[C:28]([C:27]2[C:23]([CH3:45])([CH3:22])[CH2:24][CH2:25][CH:26]=2)[CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of triphenylphosphine (0.13 g, 0.51 mmol) in DCM (1.0 mL), was slowly added bromine (0.081 g, 0.51 mmol, 0.25 mL, 2M in CCl4) at 0° C. The resulting mixture was stirred at 0° C. for 15 minutes and then a mixture of compound T2.6 (0.15 g, 0.46 mmol) and anhydrous pyridine (0.041 mL, 0.51 mmol) in DCM (3.0 mL) was added to the mixture. The reaction mixture was stirred at room temperature for 2 hours. DCM (80 mL) was added, and the mixture was washed with water (20×2 mL), and dried over Na2SO4. The solvent was removed under reduced pressure to provide product T2.7. 1H NMR (400 MHz, CDCl3) δ ppm. 7.16-7.29 (m, 3H), 6.88 (t, 1H), 6.72 (m, 2H), 5.45 (s, 1H), 4.46 (s, 2H), 3.68 (s, 3H), 2.16-2.19 (m, 2H), 1.59 (t, 2H), 0.78 (s, 6H).

Workup

customat 0° C
additionwas added to the mixture
stirringThe reaction mixture was stirred at room temperature for 2 hours
washthe mixture was washed with water (20×2 mL)
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customto provide product T2.7

Sources & evidence

ORD record: ord-8b5e4ffc6c0e495abdd7fb6a20815b82
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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