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

HRID 1400775Notes

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]([CH3:32])=[C:28](I)[CH:27]=1>CO>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[C:30]([C:3]2[C:4]([OH:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:31]=1

Participants

Conditions

Temperature: 105 °C

Procedure

(2-Chloro-6-hydroxyphenyl)boronic acid (250 mg, 1.450 mmol, 1 equiv), Pd(PPPh3)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 (2 mL) in a sealed microwave tube. 4-Bromo-2-iodo-1-methylbenzene (431 mg, 1.450 mmol, 1.0 equiv) in MeOH (1.00 mL) was to the above mixture. The mixture was heated at 105° C. overnight. Then, the crude reaction mixture was loaded on 12 g column and purified at 30% EtOAc/hexane to afford 5′-bromo-6-chloro-2′-methyl-[1,1′-biphenyl]-2-ol (345 mg, 80%). LCMS (M+1)=299.0.

Workup

customThen, the crude reaction mixture
custompurified at 30% EtOAc/hexane

Sources & evidence

ORD record: ord-140571f3bb8f4b80aa60bea10d090aa8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906929B2

Reaction notes

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