Sodium Carbonate → 2-Bromo-6-fluoro-3'-methylbiphenyl

HRID 2266259Notes

Reaction equation

HRID 2266259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1I.C([O-])([O-])=O.[Na+].[Na+].[CH3:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.C(O)C.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>[Br:1][C:2]1[C:3]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:16])[CH:22]=2)=[C:4]([F:8])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 27831271-Bromo-3-fluoro-2-iodobenzene

Product 1

HCID 593830242-Bromo-6-fluoro-3'-methylbiphenyl

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Pd(Ph3P)4 in a 500-mL round-bottom flask under N2 atmosphere was treated sequentially with a solution of 1-bromo-3-fluoro-2-iodo-benzene (30 g, 0.1 mol) in toluene (250 mL), a solution of 2N aq Na2CO3 (200 mL) and 3-methyl phenylboronic acid in ethanol (62 mL). This mixture was heated at reflux under N2 for 12 h, then cooled to rt. The mixture was partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, evaporated and purified by column chromatography to give 6-bromo-2-fluoro-3′-methyl-biphenyl (12 g). 1H NMR (400 MHz, CD3OD): 7.03 (m, 2H), 7.48-7.04 (m, 4H), 7.50 (d, 1H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux under N2 for 12 h
  3. customThe mixture was partitioned between water and EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-f116ad0ff57648489911d812e2093c58
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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