Boron tribromide → 2',3',4',5',6'-Pentafluoro-5-methyl-[1,1'-biphenyl]-2-ol
Reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[O:23]C>ClCCl>[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[C:16]1[C:17]([OH:23])=[CH:18][CH:19]=[C:20]([CH3:22])[CH:21]=1Participants
Procedure
A 1.0 M boron tribromide solution in dichloromethane (67.3 mL, 67.3 mmol, 2 equiv) was added dropwise, at −78° C., over 30 minutes to a solution of compound 6 (9.7 g, 33.65 mmol, 1 equiv) in anhydrous dichloro-methane (300 mL). The reaction was warmed to room temperature, when LCMS indicated that the reaction was complete. The reaction was quenched with ice-water (200 mL). The layers were separated and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix 65-200 g column, eluting with a gradient of 0 to 20% ethyl acetate in heptanes to give 2′,3′,4′,5′,6′-pentafluoro-5-methyl-[1,1′-biphenyl]-2-ol (7) (8.15 g, 88% yield) as a light-brown oil.
Workup
- customThe reaction was quenched with ice-water (200 mL)
- customThe layers were separated
- extractionthe aqueous phase was extracted with dichloromethane (2×100 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified on an AnaLogix 65-200 g column
- washeluting with a gradient of 0 to 20% ethyl acetate in heptanes
Sources & evidence
- ORD record
- ord-88540ca72d9b435fb30ecb58cf0a1980
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952114B2
Reaction notes
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