Boron tribromide → HCID 18992061, compound

HRID 375733Notes

Reaction equation

HRID 375733 reaction equation
[OH:1][C:2]1[C:3]([CH3:16])=[C:4]([C:9]([CH2:13][CH2:14][CH3:15])=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7]C)=[O:6].B(Br)(Br)Br>C(Cl)Cl.C(OCC)(=O)C>[OH:1][C:2]1[C:3]([CH3:16])=[C:4]([C:9]([CH2:13][CH2:14][CH3:15])=[C:10]([OH:12])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 18992142HCID 18992142, compound

Product 1

HCID 18992061HCID 18992061, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.61 g of methyl 3,5-dihydroxy-2-methyl-6-propylbenzoate in 20 ml of methylene chloride were added at 0° C. within 30 minutes 50 ml of a 1M solution of boron tribromide in methylene chloride. The mixture was stirred for 5 hours at room temperature and then diluted with 100 ml of ethyl acetate. The mixture was washed with water and with brine, and the organic layer was dried over sodium sulfate and evaporated in vacuo to yield crude 3,5-dihydroxy-2-methyl-6-propylbenzoic acid.

Workup

  1. washThe mixture was washed with water and with brine
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a1a0c9c172d490aa5b8c26862c56c4d
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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