Sodium Carbonate → 2-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-ol

HRID 423504Notes

Reaction equation

HRID 423504 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])=[CH:17][C:16]=1[F:22].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:16]1[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:15]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 532196762-Fluoro-4'-(methanesulfonyl)[1,1'-biphenyl]-4-olYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Fluoro-4′-(methylsulfonyl)-4-biphenylol (0.58 g, 71%) was prepared as a white solid from [4-(methylsulfonyl)phenyl]boronic acid (0.69 g, 3.38 mmol), 4-bromo-3-fluorophenol (0.6 g, 3.05 mmol), 2M Na2CO3 (18 mL) and Pd(PPh3)4 (30 mg, 0.03 mmol) in DME (18 mL) in a manner similar to Example 1, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, 2H, J=8.3 Hz), 7.69 (d, 2H, J=7.4 Hz), 7.40-7.30 (m, 1H), 6.80-6.65 (m, 2H), 5.10 (s, 1H), 3.09 (s, 3H); LRMS (ESI), m/z 267 (M+H).

Sources & evidence

ORD record
ord-6c6f4a25efe44e36916d4325502888b1
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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