1,4-Dibromobenzene → HCID 57592479, compound

HRID 1784406Notes

Reaction equation

HRID 1784406 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][O:15][C:16]1[C:17]([S:28](F)(=[O:30])=[O:29])=[CH:18][C:19]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21][C:20]=2[CH:27]=1>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:28]([C:17]2[C:16]([O:15][CH3:14])=[CH:27][C:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:19]=3[CH:18]=2)(=[O:29])=[O:30])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 57592494HCID 57592494, compoundHCID 178418339Butyllithium

Product 1

HCID 57592479HCID 57592479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,4-dibromobenzene (0.665 g, 2.82 mmol, 2.0 eq) in dry tetrahydrofuran (7 mL) under argon at −78° C. was added butyllithium (1.25 mL 2.5M in hexanes, 3.10 mmol, 2.2 eq) dropwise over 10 min. After a further 30 min. a suspension of sulfonyl fluoride D4 (0.385 g, 1.41 mmol, 1.0 eq) was added portionwise. The resultant mixture was allowed to warm to room temperature then stirred for 2 h. The mixture was quenched with water (40 mL) then extracted twice with ethyl acetate (2×40 mL). The organic layer was washed sequentially with water (50 mL) and brine (50 mL) then dried over MgSO4 and evaporated to dryness. Purification by Biotage chromatography, eluting with 1-6% MeOH—CH2Cl2 containing 0.5% NH3 afforded the desired product D13 as a solid, 0.289 g (50%). MH+411. 1H NMR δ (CDCl3) 2.37 (3H, s), 2.55 (4H, m), 2.93 (4H, m), 3.75 (3H, s), 6.65 (1H, s), 7.60 (2H, d), 7.80 (3H, m).

Workup

  1. additionwas added portionwise
  2. customThe mixture was quenched with water (40 mL)
  3. extractionthen extracted twice with ethyl acetate (2×40 mL)
  4. washThe organic layer was washed sequentially with water (50 mL) and brine (50 mL)
  5. dry with materialthen dried over MgSO4
  6. customevaporated to dryness
  7. customPurification by Biotage chromatography
  8. washeluting with 1-6% MeOH—CH2Cl2 containing 0.5% NH3

Sources & evidence

ORD record
ord-f290ee7300f04238a1f48776ef0e0383
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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