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Cesium fluoride → 4'-Bromo-4-hydroxy-5-methoxy-biphenyl-2-carbaldehyde

HRID 2252230
Notes
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Reaction equation

HRID 2252230 reaction equation
Br[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5].[Br:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[F-].[Cs+]>COCCOC.CO.C(Cl)Cl.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:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][C:7]([OH:12])=[C:8]([O:10][CH3:11])[CH:9]=2)=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 79599(4-Bromophenyl)boronic acidHCID 6160682-Bromo-5-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 859975574'-Bromo-4-hydroxy-5-methoxy-biphenyl-2-carbaldehydeYield 61%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 6344DichloromethaneSolvent
HCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-bromo-5-hydroxy-4-methoxy-benzaldehyde (1.00 g, 4.32 mmol), 4-bromophenyl boronic acid (1.04 g, 5.18 mmol), Pd(PPh3)4 (0.250 g), and CsF (1.97 g, 12.6 mmol) in DME/MeOH (1:1, 65 mL) was heated at 70° C. overnight. The mixture was diluted with CH2Cl2 and washed with water. The organic layer was dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography eluting with hexane/CH2Cl2 (1:9) to give 0.809 g (60%) of the desired product which was carried into the next step without further purification. MS (DCI/NH3) m/z: 307.4 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/CH2Cl2 (1:9)

Sources & evidence

ORD record
ord-59f9fc2dcfa8497294e6fb5c7ec7b7fd
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07320986B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes