Hydrochloric Acid → 4-Amino-3-(bromomethyl)-2-(trifluoromethyl)benzonitrile

HRID 913561Notes

Reaction equation

HRID 913561 reaction equation
[Br:1][CH2:2][C:3]1[C:4]([C:25]([F:28])([F:27])[F:26])=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]=C(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]#[N:7].Cl>C1COCC1>[NH2:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:25]([F:27])([F:28])[F:26])[C:3]=1[CH2:2][Br:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866206803-(Bromomethyl)-4-[(diphenylmethylidene)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 674048644-Amino-3-(bromomethyl)-2-(trifluoromethyl)benzonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the diphenylmethylidene from step E (0.250 g, 0.56 mmol) in THF (4 mL) was added 2N HCl (0.4 mL). After stirring at rt for 2 h, the reaction was partitioned in EtOAc/hexanes (20 mL; 1:2). The layers were separated and the organic portion was dried (MgSO4) and concentrated. Purification by SiO2 chromatography (10-50% EtOAc in hexane2) afforded 4-amino-3-(bromomethyl)-2-(trifluoromethyl)benzonitrile (0.073 g, 50%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.61 (d, J=8.6 Hz, 1H), 6.98 (d, J=8.6 Hz, 1H), 6.82 (bs, 2H), 4.71 (s, 2H).

Workup

  1. customthe reaction was partitioned in EtOAc/hexanes (20 mL; 1:2)
  2. customThe layers were separated
  3. dry with materialthe organic portion was dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by SiO2 chromatography (10-50% EtOAc in hexane2)

Sources & evidence

ORD record
ord-cdfbd7116a6a4552b99cf169dd856c95
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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