Boron tribromide → 4-Hydroxy-2,5-dimethylbenzoic acid

HRID 471001Notes

Reaction equation

HRID 471001 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:15]([CH3:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:17])[CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[C:15]([CH3:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:17])[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 27520364-Methoxy-2,5-dimethylbenzoic acid

Product 1

HCID 236001494-Hydroxy-2,5-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide solution (1M in DCM, 7.21 mL) was added dropwise to suspension of 4-methoxy-2,5-dimethylbenzoic acid (1 g) in DCM (5 mL) at −78° C. The reaction was allowed to warm to RT and stirred overnight. The reaction was cooled to −78° C. and boron tribromide solution (1M in DCM, 7.21 mL) was added. The reaction was allowed to warm to RT and stirred overnight. The reaction was cautiously poured onto ice (˜50 mL). The resulting aqueous solution was extracted with DCM (5×50 mL). The organic solutions were combined, washed with brine (50 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled compound as a tan solid. Yield 0.75 g.

Workup

  1. temperatureThe reaction was cooled to −78° C.
  2. temperatureto warm to RT
  3. stirringstirred overnight
  4. additionThe reaction was cautiously poured onto ice (˜50 mL)
  5. extractionThe resulting aqueous solution was extracted with DCM (5×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c631db88b9ff42d59d38826e0b22ae76
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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