Boron tribromide → HCID 59627687, compound

HRID 1930114Notes

Reaction equation

HRID 1930114 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[C:7]([O:19]C)=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1>ClCCl>[Cl:5][C:6]1[C:7]([OH:19])=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59627702HCID 59627702, compound2×

Product 1

HCID 59627687HCID 59627687, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (1.068 mL, 11.30 mmol) was added dropwise to ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-4; 456 mg, 1.88 mmol) in dichloromethane (10 mL) at ambient temperature under nitrogen. The resulting orange red solution was stirred at 0° C. for 45 minutes. The reaction mixture was carefully quenched with water (25 mL), extracted with EtOAc (2×100 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford crude product as a yellow gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-hydroxy-2-methylphenyl)acetate (310 mg, 72.2%) as a colourless oil which solidified on standing.

Workup

  1. customThe reaction mixture was carefully quenched with water (25 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product as a yellow gum
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-55e2275b12ac4ae59fe69811b0132e46
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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