Water → 1-Bromo-4-(isocyanomethyl)-2-methylbenzene

HRID 1505268Notes

Reaction equation

HRID 1505268 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH:8]=O)=[CH:4][C:3]=1[CH3:12].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N+:7]#[C-:8])=[CH:4][C:3]=1[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

Product 1

HCID 584979501-Bromo-4-(isocyanomethyl)-2-methylbenzeneYield 114.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-bromo-3-methyl-benzyl)-formamide (Example 10.2) (4.3 g) in dichloromethane (70 ml) was added a solution of phosphorus oxychloride (2.8 g) in dichloromethane (15 ml) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was poured onto a mixture of ice and water (400 ml), and sodium hydrogen carbonate (saturated) (100 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-bromo-4-isocyanomethyl-2-methyl-benzene (4.52 g) as a brown oil. 1H-NMR (400 MHz, CDCl3): 7.54 (m, 1H), 7.22 (s, 1H), 7.03 (m, 1H), 4.57 (s, 2H), 2.42 (s, 3H) ppm.

Workup

  1. additionwere added
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50efad115de944229eed5ba41d0e2112
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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