Sodium Hydroxide → 2',3',4',5,5',6'-Hexafluoro-[1,1'-biphenyl]-2-ol

HRID 1847101Notes

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]([F:22])[CH:19]=[CH:18][C:17]=1[O:23]C.C(=O)(O)[O-].[Na+].[OH-].[Na+]>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]([F:22])[CH:21]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.0 M boron tribromide solution in dichloromethane (24 mL, 24 mmol, 2.4 equiv) was added dropwise over 30 minutes, at −78° C., to a solution of compound 2 (3.0 g, 10.2 mmol, 1 equiv) in dichloromethane (100 mL). The reaction was stirred at −78° C. for 3 hours, when 1H NMR indicated that the reaction was complete. The reaction was poured into saturated sodium bicarbonate (200 mL) and the pH was adjusted to 8 with 10% sodium hydroxide. The layers were separated, then 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 over silica gel (40 g), eluting with a gradient of 0 to 20% ethyl acetate in heptanes to give 2′,3′,4′,5,5′,6′-hexafluoro-[1,1′-biphenyl]-2-ol (3) (2.3 g, 80% yield) as a white solid.

Workup

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 over silica gel (40 g)
washeluting with a gradient of 0 to 20% ethyl acetate in heptanes

Sources & evidence

ORD record: ord-a2e78483a1794905bcf07807bdc8f4df
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952114B2

Reaction notes

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