1-Bromo-3,5-di-tert-butylbenzene → (Z)-4-[2-(3,5-Di-tert-butylphenyl)-2-trimethylsilanylvinyl]benzyl Alcohol

HRID 1281237Notes

Reaction equation

HRID 1281237 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:22][CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:33]1[CH:38]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:36]=[C:35]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:34]=1>>[C:43]([C:35]1[CH:34]=[C:33](/[C:27](/[Si:28]([CH3:29])([CH3:30])[CH3:31])=[CH:26]/[C:23]2[CH:22]=[CH:21][C:20]([CH2:19][OH:18])=[CH:25][CH:24]=2)[CH:38]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:36]=1)([CH3:46])([CH3:45])[CH3:44]

Participants

3

Reactant 2

HCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 102971754-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether

Product 1

HCID 23382397(Z)-4-[2-(3,5-Di-tert-butylphenyl)-2-trimethylsilanylvinyl]benzyl Alcohol

Procedure

Following General Procedure A, 4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl ether and 1-bromo-3,5-Di-tert-butylbenzene (which can be prepared by the procedure described in Komen and Bickel Synth. Commun, 1996, 26, 1693-1698) were coupled to give the title compound (Compound 32). PNMR (300 MHz, CDCl3) δ7.40 (s, 4H), 7.33 (s, 2H), 7.08 (s, 1H), 7.07(s, 1H), 4.78 (d, J=5.9 Hz, 1H), 1.41 (s, 18H), 0.00 (s, 9H).

Workup

  1. customcan be prepared by the procedure

Sources & evidence

ORD record
ord-9280129dc4a64b15bb198872053b158e
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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