Water → 3-(4-Hydroxy-3,2''-diisobutyl-2'-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionitrile

HRID 971356Notes

Reaction equation

HRID 971356 reaction equation
B(Br)(Br)Br.[CH2:5]([C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]#[N:32])=[CH:25][C:24]=3[CH2:33][CH:34]([CH3:36])[CH3:35])=[CH:19][C:18]=2[CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)[CH:12]=[CH:13][C:14]=1[O:15]C)[CH:6]([CH3:8])[CH3:7].O>C(Cl)Cl>[OH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]#[N:32])=[CH:25][C:24]=3[CH2:33][CH:34]([CH3:36])[CH3:35])=[CH:19][C:18]=2[CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)=[CH:10][C:9]=1[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 225652343-(3,2''-Diisobutyl-4-methoxy-2'-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionitrile

Product 1

HCID 225652243-(4-Hydroxy-3,2''-diisobutyl-2'-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.44 ml (1.44 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 270.8 mg (0.48 mmol) 3-(3,2″-Diisobutyl-4-methoxy-2′-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (68) in 25 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 60 min at 0° C. and then for 12 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 261.9 mg (0.48 mmol, 98.89%) 3-(4-Hydroxy-3,2″-diisobutyl-2′-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (69) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=0.53 (d, 6H, J=6.62 Hz, 2*CH3), 0.79 (d, 6H, J=6.62 Hz, 2*CH3), 1.47 (m, 1H, CH), 1.73 (m, 1H, CH), 2.24 (d, 2H, J=7.41 Hz, CH2), 2.39 (d, 2H, J=7.09 Hz, CH2), 2.58 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.90 (t, 2H, J=7.41 Hz, CH2C2CN), 4.38 (s, 2H, CH2Naphthyl), 4.58 (s, 1H, OH), 6.76 (d, 1H, J=8.04 Hz), 6.97 (m, 2H), 7.00 (m, 1H), 7.08-7.16 (m, 5H), 7.30-7.41 (m, 4H), 7.67 (dm, 1H, J=8.04 Hz), 7.72 (dm, 1H, J=8.51 Hz), 7.78 (dm, 1H, J=8.04 Hz). MS (EI): m/z=553 (11), 552 (43), 551 (100), 141 (49). HR-MS (EI): Calcd. for C40H41NO: 551.318814. Found: 551.318350.

Workup

  1. waitfor 12 h at r.t
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-d5a0e7c1f5b14e4c8d6ccd49344c6d51
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

Loading…