Trifluoroacetic acid → HCID 69384846, compound

HRID 860976Notes

Reaction equation

HRID 860976 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH:20]=O)[CH:14]=2)=[C:7]([Br:22])[CH:6]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=2)=[C:7]([Br:22])[CH:6]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 87806978HCID 87806978, compound

Product 1

HCID 69384846HCID 69384846, compoundYield 46%

Procedure

A mixture of compound methyl[3,5-dibromo-4-(3-formyl-4-hydroxyphenoxy)phenyl]acetate (250 mg, 0.56 mmol) and trifluoroacetic acid (5.5 mL) was treated with triethylsilane (0.34 mL, 2.13 mmol) and the reaction mixture was stirred for 16 hours at room temperature. The reaction was concentrated and co-evaporated (toluene, dichloromethane), which gave a residue that was filtrated through a pad of silica. Purification on a column (MPLC, silica, gradient elution: n-heptane/ethyl acetate from 1:0 to 4:1) gave 110 mg (46%) of methyl[3,5-dibromo-4-(4-hydroxy-3-methyl-phenoxy)phenyl]acetate.

Workup

  1. concentrationThe reaction was concentrated
  2. customco-evaporated (toluene, dichloromethane), which gave a residue that
  3. filtrationwas filtrated through a pad of silica
  4. customPurification
  5. washon a column (MPLC, silica, gradient elution: n-heptane/ethyl acetate from 1:0 to 4:1)

Sources & evidence

ORD record
ord-4f860e48a6cf4530990093c0729154c4
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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