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Toluene → 5'-Bromo-6-chloro-2'-fluoro-[1,1'-biphenyl]-2-ol

HRID 1400778
Notes
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Reaction equation

HRID 1400778 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28](I)[CH:27]=1>CO.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:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[C:30]([C:3]2[C:4]([OH:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 54758882(2-Chloro-6-hydroxyphenyl)boronic acid

Product 1

HCID 867108315'-Bromo-6-chloro-2'-fluoro-[1,1'-biphenyl]-2-olYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 887MethanolSolvent

Conditions

Temperature
105 °C

Procedure

(2-Chloro-6-hydroxyphenyl)boronic acid (250 mg, 1.450 mmol, 1.0 equiv), Pd(PPh3)4 (168 mg, 0.145 mmol, 0.1 equiv) and aqueous Na2CO3 (2 M, 1.8 mL, 3.63 mmol, 2.5 equiv) were mixed with toluene (3 mL) in a sealed microwave tube. 4-Bromo-1-fluoro-2-iodobenzene (436 mg, 1.450 mmol) in MeOH (1.50 mL) was added to the above mixture. The mixture was heated at 105° C. overnight. Then, the reaction mixture was loaded on 12 g column and purified using 30% EtOAc/Hex to afford 5′-bromo-6-chloro-2′-fluoro-[1,1′-biphenyl]-2-ol (400 mg, 91% yield). 1H NMR (400 MHz, CDCl3) δ 7.57 (ddd, J=8.8, 4.5, 2.5 Hz, 1H), 7.47 (dd, J=6.3, 2.5 Hz, 1H), 7.24 (t, J=8.2 Hz, 1H), 7.17-7.06 (m, 2H), 6.90 (d, J=8.0 Hz, 1H). LCMS (M+1)=302.9.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-19daac34860a47089e1a48afd8595752
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906929B2

Reaction notes

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