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

HRID 1254310Notes

Reaction equation

HRID 1254310 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 atmosphore 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 (400MHz, 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-1668e518814d4ae39035c90122092424
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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