(4-Bromo-3,5-dimethyl-phenoxy)triisopropylsilane → HCID 66642766, compound

HRID 1170981Notes

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:20].C([Li])CCC.[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][C:28]=1[C:35]([CH3:37])=[CH2:36]>C1COCC1.CCOC(C)=O>[CH3:20][C:3]1[CH:4]=[C:5]([O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])[CH:6]=[C:7]([CH3:8])[C:2]=1[CH:31]([C:30]1[CH:33]=[CH:34][C:27]([F:26])=[C:28]([C:35]([CH3:37])=[CH2:36])[CH:29]=1)[OH:32]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-bromo-3,5-dimethyl-triisopropylsilanoxybenzene (1.29 g, 3.6 mmol, G. Chiellini et al. Biorg. Med. Chem. Lett. 2000, 10, 2607) in THF at −78° C. was added n-butyllithium (1.58 mL, 3.96 mmol, 2.5 M in THF). After 30 min, a solution of 4-fluoro-3-isopropenylbenzaldehyde (500 mg, 3.0 mmol) in THF was added. The reaction mixture was stirred at −78° C. for 1 h, allowed to warm to room temperature, diluted with EtOAc and quenched with water. The organic layer was dried over MgSO4, filtered and concentrated to afford crude 1-(2,6-dimethyl-4-triisopropylsilanyloxyphenyl)-1-(4′-fluoro-3′-isopropenylphenyl)methanol as an oil: 1H NMR (200 MHz, CDCl3): δ 7.18 (m, 1 H), 7.02 (m, 1 H), 6.94 (m, 1 H), 6.56 (s, 2 H), 6.22 (s, 1 H), 5.18 (m, 2 H), 2.20 (s, 6 H), 2.08 (s, 3 H), 1.25 (m, 3 H), 1.11 (m, 18).

Workup

temperatureto warm to room temperature
customquenched with water
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2a7c4ca5f5ac4ef48080fb25ed9af7f3
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829552B2

Reaction notes

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