Trifluoroborane-methyl sulfide → HCID 69384518, compound

HRID 860974Notes

Reaction equation

HRID 860974 reaction equation
B(F)(F)F.S(C)C.C[O:9][C:10](=[O:29])[CH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)=[C:14]([Br:28])[CH:13]=1>ClCCl>[Br:18][C:16]1[CH:17]=[C:12]([CH2:11][C:10]([OH:29])=[O:9])[CH:13]=[C:14]([Br:28])[C:15]=1[O:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 15495991HCID 15495991, compound

Product 1

HCID 69384518HCID 69384518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BF3—SMe2 (24 mL, 228 mmol) was added to a stirred solution of methyl[3,5-dibromo-4-(4-methoxyphenoxy)phenyl]acetate (2.5 g, 5.8 mmol) and dichloromethane (50 mL) at 0° C. The reaction mixture was stirred for 20 hours at room temperature and subsequently quenched with ice water (50 mL). The two layers were separated with a phase separator and the remaining water phase was extracted with ethyl acetate. Filtration through a silica pad gave the crude 3,5-dibromo-4-(4-hydroxyphenoxy)phenylacetic acid. The residue was dissolved in methanol (40 mL) and thionyl chloride (4 mL) was added carefully to the reaction. After 1.5 hours of heating at reflux, the organic phase was removed in vacuo and the residue was dissolved in chloroform. The organic phase was washed with water and concentrated to give methyl[3,5-dibromo-4-(4-hydroxyphenoxy)phenyl]acetate as beige solid (1.8 g, 75%).

Workup

  1. customsubsequently quenched with ice water (50 mL)
  2. customThe two layers were separated with a phase separator
  3. extractionthe remaining water phase was extracted with ethyl acetate
  4. filtrationFiltration through a silica pad

Sources & evidence

ORD record
ord-6f5f9854c6444573b55ada3f23b33434
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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