Hydrochloric Acid → HCID 66611706, compound

HRID 2204702Notes

Reaction equation

HRID 2204702 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:16]C)[CH:3]=1.B(Br)(Br)Br.Cl>ClCCl>[OH:16][C:4]1[CH:3]=[C:2]([CH3:1])[C:11]([C:12]([F:13])([F:14])[F:15])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 66611961HCID 66611961, compound

Product 1

HCID 66611706HCID 66611706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-methyl-2-(methyloxy)-5-(trifluoromethyl)benzoate (may be prepared as described in Description 44; 1.76 g, 7.09 mmol) in dichloromethane (70 ml) at 0° C. was added BBr3 (14.89 ml, 14.89 mmol). The solution was stirred for 2 hours, 2M HCl (30 ml) was added and the organic layer removed in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (20 ml). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 3:1 cyclohexane/ethyl acetate) to give the title compound as an oil. 1.37 g.

Workup

  1. customthe organic layer removed in vacuo
  2. customThe residue was partitioned between water (10 ml) and ethyl acetate (20 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography (SiO2, 3:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-f34f93b0fff54d8b8e1bd3e9e5ef2228
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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