Methanol → Methyl 4'-hydroxy-3'-methyl[1,1'-biphenyl]-3-carboxylate

HRID 393268Notes

Reaction equation

HRID 393268 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)=[CH:9][C:8]=1[CH3:23].CO>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)=[CH:9][C:8]=1[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 22648855HCID 22648855, compound

Product 1

HCID 22648853Methyl 4'-hydroxy-3'-methyl[1,1'-biphenyl]-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1.0 M BBr3 solution in CH2Cl2 (3.4 mL, 3.40 mmol) was added to an ice-cold solution of methyl 4′-methoxy-3′-methyl-[1,1′-biphenyl]-3-carboxylate (345 mg, 1.35 mmol) in CH2Cl2 (13 mL). The reaction mixture was stirred at 25° C. for 2 h then was cooled to 0° C. MeOH (5 mL) was added and the mixture was stirred at 0° C. for 15 min then was extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane, 10 to 15%) to yield the title compound (278 mg, 85% yield) as a white solid.

Workup

  1. temperaturethen was cooled to 0° C
  2. stirringthe mixture was stirred at 0° C. for 15 min
  3. extractionthen was extracted with CH2Cl2 (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (EtOAc:Hexane, 10 to 15%)

Sources & evidence

ORD record
ord-015ff9aacd2242dbaba6beda7e5a5565
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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