Tetrahydrofuran → HCID 86630554, compound

HRID 1454232Notes

Reaction equation

HRID 1454232 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.[Li]CCCC.C1C[O:22][CH2:21]C1>>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=1[F:13])[CH:21]=[O:22]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 86630554HCID 86630554, compoundYield 87%

Procedure

To a −78° C. solution of 2-(5-bromo-2-fluoro-phenyl)-[1,3]dioxolane (1.024 g, 4.047 mmol) in THF (40 mL) was added 2.5 M n-BuLi (1.80 mL, 4.45 mmol). After 20 min, the reaction was quenched with DMF (1.60 mL). After stirring for 1 h, the mixture was diluted with DCM, washed with a satd. aq. NaHCO3, dried (MgSO4), and concentrated. Purification by FCC (EtOAc/hexanes) gave the desired product (406.5 mg, 87%) as a white solid. 1H NMR (acetone-d6): 10.05 (s, 1H), 8.17-8.09 (m, 1H), 8.06-7.97 (m, 1H), 7.43-7.33 (m, 1H), 6.10-6.04 (m, 1H), 4.19-4.11 (m, 2H), 4.08-4.00 (m, 2H).

Workup

  1. customthe reaction was quenched with DMF (1.60 mL)
  2. additionthe mixture was diluted with DCM
  3. washwashed with a satd
  4. dry with materialaq. NaHCO3, dried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by FCC (EtOAc/hexanes)

Sources & evidence

ORD record
ord-84bebb210d714b748a46c359b1682632
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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