Bromine → HCID 59135186, compound

HRID 1028634Notes

Reaction equation

HRID 1028634 reaction equation
[Br:1]Br.[F:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:5]=1[CH:14]([CH3:16])[CH3:15].C([O-])(=O)C.[K+]>C(O)(=O)C.O.[O-]S([O-])=O.[Na+].[Na+]>[Br:1][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:4]([F:3])[C:5]=1[CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 66716980HCID 66716980, compound

Product 1

HCID 59135186HCID 59135186, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 24437Sodium SulfiteSolvent

Procedure

Bromine (80.6 mg, 26 μL, 0.504 mmol) was added to a solution of 2-fluoro-1-isopropyl-3,4-dimethoxybenzene (50.0 mg, 0.252 mmol) and potassium acetate (49.5 mg, 0.504 mmol) in acetic acid (1 mL) at room temperature and the reaction was stirred overnight. The reaction was diluted with water (10 mL) and saturated Na2SO3 (10 mL), then extracted with EtOAc (3×20 mL). The combined extracts were washed with saturated NaHCO3 (2×10 mL), dried (MgSO4) and concentrated in vacuo to afford 1-bromo-3-fluoro-2-isopropyl-4,5-dimethoxybenzene. 1H NMR (600 MHz, CDCl3) δ 6.86 (d, J=2.0 Hz, 1H), 3.87 (s, 3H), 3.81 (s, 3H), 3.43-3.34 (m, 1H), 1.31-1.29 (dd, J=7.1, 1.4 Hz, 6H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined extracts were washed with saturated NaHCO3 (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-859b3d064b83400585254edd43c441d2
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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