Hydrochloric Acid → HCID 69385467, compound

HRID 860977Notes

Reaction equation

HRID 860977 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:25])[CH2:6][C:7]1[CH:12]=[C:11]([Br:13])[C:10]([O:14][C:15]2[CH:20]=[C:19]([Br:21])[C:18]([OH:22])=[C:17]([Br:23])[CH:16]=2)=[C:9]([Br:24])[CH:8]=1.Cl>O1CCCC1>[Br:13][C:11]1[CH:12]=[C:7]([CH2:6][C:5]([OH:25])=[O:4])[CH:8]=[C:9]([Br:24])[C:10]=1[O:14][C:15]1[CH:16]=[C:17]([Br:23])[C:18]([OH:22])=[C:19]([Br:21])[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69387063HCID 69387063, compound

Product 1

HCID 69385467HCID 69385467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of methyl[3,5-dibromo-4-(3-formyl-4-hydroxy-5-methyl-phenoxy)phenyl]acetate (60 mg, 0.13 mmol) and trifluoroacetic acid (1.5 mL), triethylsilane (62 μl, 0.39 mmol) was added. The reaction mixture was stirred at room temperature for 20 hours, the organic phase concentrated and the residue was co-evaporated (toluene) to give 60 mg of crude methyl[3,5-dibromo-4-(3,5-dibromo-4-hydroxyphenoxy)phenyl]acetate. The crude product was used in next step. Lithium hydroxide (1.5 ml, 1N) was added to a stirred solution of crude methyl[3,5-dibromo-4-(3,5-dibromo-4-hydroxyphenoxy)phenyl]acetate and tetrahydrofuran (1.5 mL). The resulting mixture was stirred for 2 hours at room temperature, acidified with hydrochloric acid (1 N) and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified on column (HPLC, C8, gradient eluent: acetonitrile/water (0.5% formic acid) from 1:4 to 1:0) to give 16 mg (14% for both steps) of 3,5-dibromo-4-(3,5-dibromo-4-hydroxyphenoxy)phenylacetic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on column (HPLC, C8, gradient eluent: acetonitrile/water (0.5% formic acid) from 1:4 to 1:0)

Sources & evidence

ORD record
ord-3ff028f911e843b3b0710b82386e2ec2
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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