Water → 7-Bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

HRID 1177186Notes

Reaction equation

HRID 1177186 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Br:11])=[C:6]([OH:12])[C:5]=1[CH2:13][C:14]([CH3:16])=[CH2:15].B(F)(F)F.CCOCC.O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Br:11])=[C:6]2[O:12][C:14]([CH3:16])([CH3:15])[CH2:13][C:5]=12)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 595603784-Bromo-3,5-dihydroxy-2-(2-methyl-allyl)-benzoic acid methyl ester

Product 1

HCID 595601447-Bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-3,5-dihydroxy-2-(2-methyl-allyl)-benzoic acid methyl ester (197c) (85 g, 0.28 mol) in CH2Cl2 (1500 mL) was added drop wise BF3.Et2O (180 mL, 1.41 mol) at 0° C. The mixture was stirred at room temperature for 2 hr. After TLC (petroleum ether/EtOAc=5/1) showed the reaction was complete, the reaction mixture was poured into water (1 L). The organic phase was separated and washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated to give a yellow solid. The crude solid was purified by column chromatography (petroleum ether/EtOAc=15/1) to give the title compound (37 g, 44% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.07 (s, 1H), 5.43 (s, 1H), 3.80 (s, 3H), 3.29 (s, 2H), 1.45 (s, 6H)

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customThe crude solid was purified by column chromatography (petroleum ether/EtOAc=15/1)

Sources & evidence

ORD record
ord-24869e4aa78c4a908b23d5e755203d35
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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