Trifluoroacetic acid → HCID 59678428, compound

HRID 1392564Notes

Reaction equation

C([SiH](CC)CC)C.[Br:8][C:9]1[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([N+:32]([O-:34])=[O:33])[CH:25]=[C:24]([Br:35])[C:10]=1[O:11][C:12]1[CH:13]=[C:14]([CH:21]([CH3:23])[CH3:22])[C:15]([OH:20])=[C:16]([CH:19]=1)[CH:17]=O.C(O)(C(F)(F)F)=O>>[Br:8][C:9]1[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([N+:32]([O-:34])=[O:33])[CH:25]=[C:24]([Br:35])[C:10]=1[O:11][C:12]1[CH:13]=[C:14]([CH:21]([CH3:23])[CH3:22])[C:15]([OH:20])=[C:16]([CH3:17])[CH:19]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 59678431HCID 59678431, compound

Product 1

HCID 59678428HCID 59678428, compoundYield 99%

Procedure

Triethylsilane (115 mg, 0.99 mmol) was added to 5-(2,6-dibromo-4-nitro-3-trifluoromethylphenoxy)-2-hydroxy-3-isopropylbenzaldehyde of Part 11D (130 mg, 0.25 mmol) and stirred at room temperature for two minutes. TFA (6 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc) to give 133 mg (99%) of 4-(2,6-dibromo-4-nitro-3-trifluoromethylphenoxy)-2-methyl-6-isopropylphenol.

Workup

stirringthe reaction mixture was stirred at room temperature for 16 hours
concentrationThe reaction mixture was concentrated
customthe residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc)

Sources & evidence

ORD record: ord-bc92ffa6bd4d4f779106324fcd793e3e
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342127B2

Reaction notes

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