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

HRID 971344Notes

Reaction equation

HRID 971344 reaction equation
B(Br)(Br)Br.[CH2:5]([C:12]1[CH:13]=[C:14]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]#[N:42])=[CH:35][C:34]=2[CH2:43][CH:44]([CH3:46])[CH3:45])[CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[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:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]#[N:42])=[CH:35][C:34]=2[CH2:43][CH:44]([CH3:46])[CH3:45])[CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 121347133-(3',3''-Dibenzyl-2-isobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrile

Product 1

HCID 121347143-(3',3''-Dibenzyl-4''-hydroxy-2-isobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrileYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.90 ml (0.90 mmol, 3 eqv) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 164.3 mg (0.30 mmol) 3-(3′,3″-Dibenzyl-2-isobutyl-4″-methoxy-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (27) in 7 ml dry CH2Cl2 at 0° C. via syringe. After that, the solution was stirred for 2 h at 0° C. and then for 4 h at rt. 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 137.5 mg (0.26 mmol, 86%) 28 as a colorless oil: Rf (Hexanes/EtOAc (2+1)) 0.35; 1H NMR (500 MHz, CDCl3) δ 0.67 (d, 6H, J=6.62 Hz), 1.61 (m, 1H), 2.40 (d, 2H, J=7.09 Hz), 2.58 (t, 2H, J=7.41 Hz), 2.91 (t, 2H, J=7.41 Hz), 3.89 (s, 2H), 3.93 (s, 2H), 5.57 (s, 1H), 6.74 (d, 1H, J=8.04 Hz), 6.90 (m, 2H), 6.99-7.26 (m, 16H); LRMS (EI) m/z 536 (19), 535 (46), 501 (10), 446 (9), 369 (21), 91 (100), 78 (12), 76 (10); HRMS (EI) Calcd. for C39H37NO: 535.287514. Found: 535.287420.

Workup

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

Sources & evidence

ORD record
ord-869a7ebb302842adb5bd12f48ebf8e48
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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