Carbon tetrabromide → 1,1-Dibromo-2-{3,5-bis[2-(3,5-di-tert-butylphenyl)vinyl]phenyl}ethene

HRID 495218Notes

Reaction equation

HRID 495218 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][C:36]2[CH:37]=[C:38]([CH:41]=[C:42]([CH:44]=[CH:45][C:46]3[CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:49]=[C:48]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH:47]=3)[CH:43]=2)[CH:39]=O)[CH:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=1)([CH3:23])([CH3:22])[CH3:21].[C:60]([Br:64])(Br)(Br)[Br:61]>ClCCl>[Br:61][C:60]([Br:64])=[CH:39][C:38]1[CH:41]=[C:42]([CH:44]=[CH:45][C:46]2[CH:51]=[C:50]([C:52]([CH3:53])([CH3:54])[CH3:55])[CH:49]=[C:48]([C:56]([CH3:59])([CH3:57])[CH3:58])[CH:47]=2)[CH:43]=[C:36]([CH:35]=[CH:34][C:26]2[CH:25]=[C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=2)[CH:37]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 540286873,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

Product 1

HCID 865927481,1-Dibromo-2-{3,5-bis[2-(3,5-di-tert-butylphenyl)vinyl]phenyl}etheneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (3.92 g, 14.96 mmol) was added in one portion to a stirred solution of -3,5-bis[2-(3,5-di-tert-butylphenyl)vinyl]benzaldehyde (1) (2.00 g, 3.74 mmol) and carbon tetrabromide (2.48 g, 7.38 mmol) in dichloromethane (20 mL). Heat was evolved and the mixture stirred at room temperature for 75 min. The resultant orange suspension was washed with water (2×50 mL), dried over anhydrous magnesium sulphate, filtered and the solvent removed to leave an orange-brown residue, which was purified by passing through a plug of silica with dichloromethane—light petroleum (2:3) as eluent. The solvent was removed to give 2-{3,5-bis[2-(3,5-di-tert-butylphenyl)vinyl]phenyl}-1,1-dibromoethene (2) as a white foam (2.45 g, 95%) mp 148-150° C. (Found: C, 69.5; H, 7.3; C40H50Br2 requires C, 69.6; H, 7.3%); νmax(KBr)/cm−1 1595 (C═C) and 958 (C═C—H trans); λmax(CH2Cl2)/nm 306 (log(ε/dm3 mol−1 cm−1)4.85), 317 (4.85) and 329sh (4.73); −δH(400 MHz, CDCl3) 1.40 (36 H, s, t-butyl), 7.14 and 7.24 (4 H, d, J 16, vinyl H) 7.40 (2 H, dd, J 1.5, sp H),7.42(4 H, d, J 1.5, sp H), 7.56 (1 H, s, CHCBr2), 7.60 (2 H, s, cp H) and 7.69 (1 H, s, cp H); m/z (CI+) 692.2 (MH+, 100%), 613.2 (M−79Br, 96%), 611.2 (M−81Br, 90%) and 533.3 (M−279Br, 74%).

Workup

  1. temperatureHeat
  2. washThe resultant orange suspension was washed with water (2×50 mL)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto leave an orange-brown residue, which
  7. customwas purified
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-330fb94fdb904f009f35133748040f8a
Source dataset
uspto-grants-2009_05
Patent number
US07537842B2

Reaction notes

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