Water → HCID 22565244, compound

HRID 25847

Reaction equation

HRID 25847 reaction equation
B(Br)(Br)Br.[CH2:5]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]#[N:24])=[CH:17][C:16]=2[CH2:25][CH:26]([CH3:28])[CH3:27])[CH:12]=[CH:11][C:10]=1[C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[C:31]([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:30]=1)[CH:6]([CH3:8])[CH3:7].O>C(Cl)Cl>[OH:35][C:32]1[CH:33]=[CH:34][C:29]([C:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]#[N:24])=[CH:17][C:16]=3[CH2:25][CH:26]([CH3:27])[CH3:28])=[CH:14][C:9]=2[CH2:5][CH:6]([CH3:8])[CH3:7])=[CH:30][C:31]=1[CH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 225652543-(2',2''-Diisobutyl-4-methoxy-3-naphthalen-1-ylmethyl-[1,1':4', 1'']-terphenyl-4''-yl)propionitrile

Product 1

HCID 22565244HCID 22565244, compoundYield 62.85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.02 ml (1.02 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 192.9 mg (0.34 mmol) 3-(2′,2″-Diisobutyl-4-methoxy-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (76) in 20 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 3 h 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 117.9 mg (0.21 mmol, 62.85%) 3-(4-Hydroxy-2′,2″-diisobutyl-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]terphenyl-4″-yl)propionitrile (32) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.37. 1H-NMR (500 MHz, CDCl3): δ=0.59 (d, 6H, J=6.62 Hz, 2*CH3), 0.70 (d, 6H, J=6.78 Hz, 2*CH3), 1.50 (m, 1H, CH), 1.65 (m, 1H, CH), 2.32 (d, 2H, J=7.25 Hz, CH2), 2.47 (d, 2H, J=7.25 Hz, CH2), 2.62 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.94 (t, 2H, J=7.41 Hz, CH2CH2CN), 4.47 (s, 2H, CH2Naphthyl), 480 (s, 1H, OH), 6.86 (d, 1H, J=8.36 Hz), 6.98-7.16 (m, 9H), 7.38 (m, 1H), 7.43-7.48 (m, 2H), 7.73 (dm, 1H, J=8.73 Hz), 7.83 (m, 1H), 8.06 (m, 1H). MS (EI): m/z=552 (30), 551 (65), 446 (21), 419 (21), 178 (19), 155 (15), 149 (24), 142 (18), 141 (100), 128 (28), 97 (23), 85 (26), 83 (25), 71 (39), 69 (30), 57 (74), 55 (35). HR-MS (EI): Calcd. for C40H41NO: 551.318814. Found: 551.318768.

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-19b39617ccb74e98a116d56ba23727a3
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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