Boron tribromide → HCID 10131175, compound

HRID 1940216Notes

Reaction equation

HRID 1940216 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([CH3:23])=[C:9]([CH3:22])[C:10]2[O:14][C:13]([CH3:16])([CH3:15])[CH:12]([C:17]([OH:19])=[O:18])[C:11]=2[C:20]=1[CH3:21]>ClCCl>[OH:6][C:7]1[C:8]([CH3:23])=[C:9]([CH3:22])[C:10]2[O:14][C:13]([CH3:16])([CH3:15])[CH:12]([C:17]([OH:19])=[O:18])[C:11]=2[C:20]=1[CH3:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 53912933HCID 53912933, compound

Product 1

HCID 10131175HCID 10131175, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.42 mL of 1M solution in dichloromethane, 0.42 mmol) is added dropwise at -78° C. and under nitrogen to a solution of 5-methoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid (100 mg, 0.38 mmol) in dichloromethane (4 mL). The reaction mixture is allowed to warm to room temperature and stirred overnight. The reaction is quenched by addition of water (10 mL) and extracted with dichloromethane (2×20 mL). The organic phase is dried (magnesium sulfate) and evaporated to dryness to give 90 mg (95%) of 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid as a white solid. A sample is recrystallized in heptane/ethyl acetate, mp=182°-184° C.

Workup

  1. customThe reaction is quenched by addition of water (10 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. dry with materialThe organic phase is dried (magnesium sulfate)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2e7784db65a34c599dfdc318dcfe7c9f
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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