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Cesium carbonate → 5'-Bromo-4-(ethylsulfonyl)-2,2'-dimethoxy-1,1-biphenyl

HRID 1846036
Notes
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Reaction equation

HRID 1846036 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4](I)[CH:3]=1.[CH2:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[C:18]([O:31][CH3:32])[CH:17]=1)(=[O:15])=[O:14])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:19]2[CH:20]=[CH:21][C:16]([S:13]([CH2:11][CH3:12])(=[O:15])=[O:14])=[CH:17][C:18]=2[O:31][CH3:32])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 109799044-Bromo-2-iodo-1-methoxybenzeneHCID 867232082-(4-(Ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 867232595'-Bromo-4-(ethylsulfonyl)-2,2'-dimethoxy-1,1-biphenylYield 45%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-bromo-2-iodo-1-methoxybenzene (Preparation 57, 350 mg, 1.12 mmol), 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 365 mg, 1.12 mmol) and aqueous caesium carbonate solution (1M, 2.23 mL, 2.23 mmol) in dioxane (18 mL) was degassed with nitrogen for 10 min, followed by addition of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (46.0 mg, 0.0056 mmol). The resulting mixture was heated at 80° C. for 16 hours. After cooling to room temperature and concentration in vacuo, the crude residue was partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The organic layers were combined and washed with brine (25 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptanes/EtOAc (70:30), to afford the title compound as off-white solid in 45% yield, 150 mg.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationconcentration in vacuo
  3. customthe crude residue was partitioned between water (30 mL) and EtOAc (30 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. washwashed with brine (25 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with heptanes/EtOAc (70:30)

Sources & evidence

ORD record
ord-0e5d24f2ee2444a9a172268d609a667d
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952008B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes