3-Fluoro-4-methoxyphenylboronic acid → HCID 10546170, compound

HRID 1598832Notes

Reaction equation

HRID 1598832 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>>[F:18][C:19]1[CH:20]=[C:21]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

3

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 10710131HCID 10710131, compound

Product 1

HCID 10546170HCID 10546170, compoundYield 88%

Procedure

Following the general procedure outlined in Synthetic Scheme VI, 5.0 g (16 mmol) of 1-bromo-2-[4-(methylsulfonyl)phenyl]benzene (Step 2) was reacted with 4.1 g (24 mmol) of 3-fluoro-4-methoxyphenylboronic acid (Step 3). Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (35:65) and subsequent recrystallization from ethyl acetate/hexane gave 4.82 g (88%) of 2-fluoro-1-methoxy-4-[2-[4-(methylsulfonyl)phenyl]phenyl]benzene as a colorless solid:

Workup

  1. customPurification by silica gel chromatography (Waters Prep-500A)
  2. customwith ethyl acetate/hexane (35:65) and subsequent recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3b810bfb834a484db10833ebc57930be
Source dataset
uspto-grants-1998_04
Patent number
US05739166

Reaction notes

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