Sodium Carbonate → 4-Bromo-4'-(diphenylamino)biphenyl

HRID 1422461

Reaction equation

HRID 1422461 reaction equation
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.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:30][C:27]1[CH:28]=[CH:29][C:24]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 113155504-Bromo-4'-(diphenylamino)biphenylYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo-1-bromobenzene (1.33 g, 4.71 mmol), Na2CO3 (1.78 g, 16.8 mmol) and Pd(PPh3)4 (0.163 g, 0.141 mmol) in THF/H2O (28 mL/17 mL) was degassed and the resulting mixture was heated at reflux overnight under an argon atmosphere. After cooling, the mixture was poured into dichloromethane (150 mL), then washed with water (2×150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, purified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1) then recrystallized in dichloromethane/methanol to afford a white solid (Compound 35)(1.64 g, in 87% yield).

Workup

  1. customwas degassed
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux overnight under an argon atmosphere
  4. temperatureAfter cooling
  5. additionthe mixture was poured into dichloromethane (150 mL)
  6. washwashed with water (2×150 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. custompurified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1)
  9. customthen recrystallized in dichloromethane/methanol

Sources & evidence

ORD record
ord-3ec6cdd74f694e62ac0de91d7d5ef30e
Source dataset
uspto-grants-2015_01
Patent number
US08927121B2

Linked notes

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