Methanol → Methyl 5-bromo-[1,1'-biphenyl]-2-carboxylate

HRID 1499123Notes

Reaction equation

HRID 1499123 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:21]O>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]([O:16][CH3:21])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 234361085-Bromo-[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 54332024Methyl 5-bromo-[1,1'-biphenyl]-2-carboxylate

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-[1,1′-biphenyl]-2-carboxylic acid (5 g, 18.2 mmol) in MeOH (30 mL) was added SOCl2 (10 mL) dropwise. The reaction mixture was heated to 70° C. for 2 h, then cooled to RT. The mixture was concentrated, adjusted to pH=7-8 with saturated aqueous NaHCO3 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and purified by normal phase silica gel column (EtOAc/PE 50:1) to afford methyl 5-bromo-[1,1′-biphenyl]-2-carboxylate as a colorless oil.

Workup

  1. temperaturecooled to RT
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by normal phase silica gel column (EtOAc/PE 50:1)

Sources & evidence

ORD record
ord-b53a5e62e5b6433fac2cbd7bb16d1203
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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