Water → (5-Bromo-2-fluoro-phenyl)-{4-[(triisopropylsilyl)-ethynyl]-phenyl}methanol

HRID 2106413Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=1)[CH:31]=[O:32].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:31]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:32])[CH:33]=1

Participants

Conditions

Temperature: -78 °C

Procedure

33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phase are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1).

Workup

additionare added dropwise over 15 min
waitThe resulting solution is left in the cooling bath
temperatureto warm up overnight to ambient temperature
extractionthe mixture is extracted with ethyl acetate
dry with materialThe combined organic phase are dried over sodium sulphate
customthe solvent is removed
customThe residue is purified through silica gel (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-0cdab6fdac004177b7a929c51952fbf4
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579449B2

Reaction notes

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