Sodium Sulfite → HCID 67982615, compound

HRID 1503112Notes

Reaction equation

HRID 1503112 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[F:11])[CH3:2].C1C(=O)N([Br:19])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+]>C(#N)C>[Br:19][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]([F:11])=[CH:5][C:6]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 543174901-Ethyl-2-fluoro-4-methoxybenzene

Product 1

HCID 67982615HCID 67982615, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-ethyl-2-fluoro-4-methoxybenzene (MET) (7.70 g, 50 mmol) was dissolved in acetonitrile (100 mL), and NBS (9.80 g, 55 mmol) was added in a single solid addition. The reaction was stirred at rt and was completed in 3-4 hours. The reaction mixture was quenched with 2M Na2SO3 (40 mL, 0.08 mol) and concentrated to ¼ of the total volume, then diluted with water (80 mL) and petroleum ether (50 mL). The organic layer was cut and washed with water (3×50 mL), 1M NaOH (50 mL), water (50 mL), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to yield 1-bromo-5-ethyl-4-fluoro-2-methoxybenzene (BrMET) as a colorless oil (11.16 g, 96%): 1H NMR (CDCl3) δ 1.19 (t, J=7.6, 3H), 2.58 (q, J=7.6, 2H), 3.85 (s, 3H), 6.61 (d, J=11.4, 1H), 7.35 (d, J=8.1, 1H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water (80 mL) and petroleum ether (50 mL)
  3. washwashed with water (3×50 mL), 1M NaOH (50 mL), water (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c9e0df90ce534236b311521d487e0576
Source dataset
uspto-grants-2015_12
Patent number
US09212118B2

Reaction notes

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