Isopropanol → 3,5-Bis(3',5'-di-tert-butylstyryl)benzyl bromide

HRID 1178174

Reaction equation

HRID 1178174 reaction equation
P(Br)(Br)[Br:2].[C:5]([C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:40]=1)[CH:12]=[CH:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH:22]=[CH:23][C:24]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=[C:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:25]=2)[CH:21]=1)[CH2:17]O)([CH3:8])([CH3:7])[CH3:6].CC(O)C>ClCCl>[C:5]([C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:40]=1)[CH:12]=[CH:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH:22]=[CH:23][C:24]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=[C:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:25]=2)[CH:21]=1)[CH2:17][Br:2])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24614Phosphorus tribromideHCID 674021763,5-Bis(3',5'-di-tert-butylstyryl)benzyl alcohol

Product 1

HCID 685452733,5-Bis(3',5'-di-tert-butylstyryl)benzyl bromideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus tribromide (2.8 cm3, 30 mmol) was added to a solution of 3,5-bis(3′,5′-di-tert-butylstyryl)benzyl alcohol (1.60 g, 3.0 mmol) in dichloromethane (50 cm3) and the mixture stirred at room temperature for 3 h. Propan-2-ol (14 cm3) was added slowly and the solvent was completely removed. The residue was purified by column chromatography over silica, eluting with dichloromethane-light petroleum (40-60) (1:9), giving 3,5-bis(3′,5′-di-tert-butylstyryl)benzyl bromide (1.52 g, 85%). A sample for analysis was recrystallised from a dichloromethane-light petroleum (60-80) mixture, mp 222-223° C. (Found: C, 77.75; H. 8.72. C39H51Br requires C, 78.11; H, 8.57%); νmax(CHCl3)/cm−1 1596 s (C═C) and 964 s (C═C—H trans); λmax(CHCl3)/nm (logε) 315 (4.82); δH(400 MHz, CDCl3) 1.38 (36 H, s, t-Bu), 4.55 (2 H, s, CH2), 7.12 and 7.24 (4 H, d, J 16, 7′,8′-H), 7.39 (2 H, dd, J 1.5, 4′-H), 7.41 (4 H, d, J 1.5, 2′,6′-H), 7.47 (2 H, d, J 1, 2,6-H) and 7.63 (1 H, m, 4-H); m/z (APCI+) 521 ((M-Br)+, 100%) and 599 (M+, 40%).

Workup

  1. customthe solvent was completely removed
  2. customThe residue was purified by column chromatography over silica
  3. washeluting with dichloromethane-light petroleum (40-60) (1:9)

Sources & evidence

ORD record
ord-76daeca91131498ca01acc9905e87ee3
Source dataset
uspto-grants-2007_10
Patent number
US07276299B2

Linked notes

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