5-Bromophthalide → Tert-butyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate

HRID 2173177Notes

Reaction equation

HRID 2173177 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[C:12]([O:16][C:17](=[O:21])[CH2:18][Zn]Cl)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[O:9]=[C:6]1[C:5]2[CH:10]=[CH:11][C:2]([CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:21])=[CH:3][C:4]=2[CH2:8][O:7]1

Participants

4

Reactant 2

HCID 6031445-BromophthalideHCID 178451184HCID 178451184, compound

Product 1

HCID 77230657Tert-butyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
105 °C

Procedure

To a 20 mL microwave tube charged with 5-bromo-2-benzofuran-1(3H)-one (500 mg, 2.35 mmol) and palladium tetrakis triphenylphosphine (136 mg, 0.117 mmol) in THF (5 mL) was added (2-tert-butoxy-2-oxoethyl) (chloro) zinc (6.57 mL, 0.5 M, 3.29 mmol). The mixture was purged with nitrogen 3 times, and heated to 105° C. for 30 minutes in a microwave reactor. The reaction mixture was poured into water and filtered then extracted with ethyl acetate twice. The organic layer was ashed with brine, dried, and evaporated to dryness. The residue was purified by MPLC on a 40 g ISCO Redi-Sep column to yield tert-butyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate. 1H-NMR (500 MHz, CDCl3) δ ppm 7.89 (d, J=7.7 Hz, 1H), 7.46 (d, J=8.3 Hz, 1H), 7.44 (s, 1H), 5.33 (s, 2H), 3.69 (s, 2H), 1.47 (s, 9H).

Workup

  1. customThe mixture was purged with nitrogen 3 times
  2. additionThe reaction mixture was poured into water
  3. filtrationfiltered
  4. extractionthen extracted with ethyl acetate twice
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by MPLC on a 40 g ISCO Redi-Sep column

Sources & evidence

ORD record
ord-bc94876e0fa14013b56f22f28db91792
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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