Sodium Carbonate → 3-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-ol

HRID 423495Notes

Reaction equation

HRID 423495 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:22])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[F:22][C:17]1[CH:16]=[C:15]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[CH:20]=[CH:19][C:18]=1[OH:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 27343644-(Methanesulfonyl)phenylboronic acid

Product 1

HCID 532196743-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-olYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Fluoro-4′-(methylsulfonyl)-4-biphenylol (0.42 g, 62%) was prepared as an off-white solid from [4-(methylsulfonyl)phenyl]boronic acid (0.58 g, 2.82 mmol), 4-bromo-2-fluorophenol (0.5 g, 2.57 mmol), 2M Na2CO3 (15 mL) and Pd(PPh3)4 (30 mg 0.03 mmol) in DME (15 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, 2H, J=8.6 Hz), 7.70 (d, 2H, J=8.5 Hz), 7.40-7.30 (m, 2H), 7.11 (t, 1H, J=8.6 Hz), 5.22 (d, 1H, J=4.1 Hz), 3.08 (s, 3H); LRMS (APCI), m/z 267 (M+H).

Sources & evidence

ORD record
ord-303b29eb39dd40e6a21f6b5d0595d1f5
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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