Water → 3-(3'-Benzyl-4''-hydroxy-2,3''-diisobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrile

HRID 25836

Reaction equation

HRID 25836 reaction equation
B(Br)(Br)Br.[CH2:5]([C:12]1[CH:13]=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]#[N:39])=[CH:32][C:31]=2[CH2:40][CH:41]([CH3:43])[CH3:42])[CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>C(Cl)Cl>[CH2:5]([C:12]1[CH:13]=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]#[N:39])=[CH:32][C:31]=2[CH2:40][CH:41]([CH3:43])[CH3:42])[CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 225652423-(3'-Benzyl-2,3''-diisobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrile

Product 1

HCID 225652293-(3'-Benzyl-4''-hydroxy-2,3''-diisobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrileYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.71 ml (0.71 mmol, 2.98 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 122.8 mg (0.238 mmol) 3-(3′-Benzyl-2,3″-diisobutyl-4″-methoxy-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (55) in 5 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 90 min at 0° C. and then for 5 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (2+1)) yielded 119.3 mg (0.24 mmol, 99.91%) 3-(3′-Benzyl-4″-hydroxy-2,3″-disobutyl-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (56) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=0.69 (d, 6H, J=6.62 Hz, 2*CH3), 0.86 (d, 6H, J=6.62 Hz, 2*CH3), 1.63 (m, 1H, CH), 1.87 (m, 1H, CH), 2.43 (d, 2H, J=7.25 Hz, CH2), 2.47 (d, 2H, J=7.09 Hz, CH2), 2.61 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.93 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.95 (s, 2H, CH2Ph), 5.51 (s, 1H, OH), 6.88 (d, 1H, J=2.05 Hz), 6.95 (m, 2H), 6.97-7.26 (m, 11H). MS (EI): m/z=502 (40), 501 (100), 458 (4), 367 (10), 327 (7), 307 (8), 263 (8), 91 (43). HR-MS (EI): Calcd. for C36H39NO: 501.303164. Found: 501.303902.

Workup

  1. waitfor 5 h at r.t
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-ef13984c5b2c428ea3a095891bcf5969
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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