Sodium Hydroxide → 1-Bromo-3-monofluoromethoxy-5-vinylbenzene
Reaction equation
[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.Br[C:17]1[CH:22]=[C:21]([O:23][CH2:24][F:25])[CH:20]=[C:19]([Br:26])[CH:18]=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:26][C:19]1[CH:18]=[C:17]([CH:1]=[CH2:2])[CH:22]=[C:21]([O:23][CH2:24][F:25])[CH:20]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Tri(butyl)vinyltin (10.0 g, 31.4 mmol) was added dropwise to a solution of 1,3-dibromo-5-monofluoromethoxybenzene (8.5 g, 29.9 mmol; see step (iii) above), tetrakis(triphenylphosphine)palladium(0) (690 mg, 0.599 mmol), and 2,6-di-tert-butyl-4-methylphenol (spatula tip) in toluene (100 mL) under nitrogen. The mixture was stirred at 70° C. for 8 h. The mixture was cooled to 0° C. and 1N NaOH (70 mL) was added. After 1 h, the mixture was extracted with CH2Cl2 (3× 300 mL) then, the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with hexanes afforded the sub-title compound (4.3 g, 57%) as a colourless oil.
Workup
- temperatureThe mixture was cooled to 0° C.
- waitAfter 1 h
- extractionthe mixture was extracted with CH2Cl2 (3× 300 mL)
- dry with materialthe combined organics were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-264ce183b6554a8ab771f8635cf31bde
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645751B2
Reaction notes
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