Boron tribromide → HCID 18329463, compound

HRID 1250088Notes

Reaction equation

HRID 1250088 reaction equation
B(Br)(Br)Br.[CH:5]([C:8]1[C:16]([O:17]C)=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])([CH3:7])[CH3:6]>ClCCl>[OH:17][C:16]1[C:8]([CH:5]([CH3:7])[CH3:6])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18329461HCID 18329461, compound

Product 1

HCID 18329463HCID 18329463, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1M boron tribromide in dichloromethane (15 mL, 15 mmol) was added dropwise to a solution of 2-isopropyl-3-methoxybenzoic acid in dichloromethane. After stirring for 2 hours, the reaction mixture was cooled to 0° C., quenched with water, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by silica gel flash chromatography, eluting with dichloromethane/methanol and 1% acetic acid, gave 3-hydroxy-2-isopropylbenzoic acid as a white crystalline solid (1.32 g, 97.5%).

Workup

  1. customquenched with water
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel flash chromatography
  7. washeluting with dichloromethane/methanol and 1% acetic acid

Sources & evidence

ORD record
ord-9cd83d8bc03c4059bce9f84d285a781e
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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