Hydrochloric Acid → HCID 57713314, compound

HRID 1983860Notes

Reaction equation

HRID 1983860 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]([N+:16]([O-:18])=[O:17])=[CH:8][C:7]=1[O:19]C.O.Cl>ClCCl>[F:5][C:6]1[CH:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[C:9]([N+:16]([O-:18])=[O:17])=[CH:8][C:7]=1[OH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25134Boron tribromideHCID 57713306HCID 57713306, compound

Product 1

HCID 57713314HCID 57713314, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1N solution of boron tribromide in dichloromethane (15 ml) was added dropwise to a solution of 1-fluoro-2-methoxy-4-nitro-5-(trifluoromethyl)benzene obtained in Reference Example 16 (1.4 g) in dichloromethane (5 ml) with ice-cooling. After stirring at room temperature overnight, water and 1N hydrochloric acid was added to the reaction mixture. After stirring for 30 minutes, an organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (developing solvent:ethyl acetate-hexane=1:3) to obtain the title compound as crystals (0.5 g, 38%).

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 30 minutes
  3. customan organic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (developing solvent:ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-7dde0b826aaa4501b92bb483b55f7d13
Source dataset
uspto-grants-2009_06
Patent number
US07541478B2

Reaction notes

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