1-Bromo-2-fluorobenzene → HCID 14157414, compound

HRID 845340Notes

Reaction equation

HRID 845340 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])CCC.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:25])[CH:22]2[O:24][CH2:23]2)=[CH:17][CH:16]=1>C1COCC1.C(OCC)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[F:8])([CH:22]2[CH2:23][O:24]2)[OH:25])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 612591-Bromo-2-fluorobenzeneHCID 14157413HCID 14157413, compoundHCID 178418339Butyllithium

Product 1

HCID 14157414HCID 14157414, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.9 g of 2-bromofluorobenzene in 10 mL of THF and 20 mL of diethyl ether was added 3.2 mL of a 1.6M solution of n-butyllithium in hexanes at -78°. After the addition was complete, a solution of 0.9 g of 4'-chloro-2,3-epoxypropiophenone (J.T. Lumb, Tetrahedron Lett., 1970, 579) in 5 mL of ether was added, and the reaction mixture was allowed to warm to room temperature. After being quenched with 10 mL of saturated NH4Cl (aqueous), the mixture was separated, the organic phase was washed with brine, dried (MgSO4), filtered, concentrated, and triturated with hexanes to afford 1.0 g of the title compound, m.p. 120°-122°.

Workup

  1. additionAfter the addition
  2. customAfter being quenched with 10 mL of saturated NH4Cl (aqueous)
  3. customthe mixture was separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customtriturated with hexanes

Sources & evidence

ORD record
ord-177df886edf843b19ea42ceee1906cd6
Source dataset
uspto-grants-1988_07
Patent number
US04758262

Reaction notes

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