Methanol → 2-(4-Chloro-3-fluorophenyl)ethylamine

HRID 1843904Notes

Reaction equation

HRID 1843904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][N+:10]([O-])=O)=[CH:4][C:3]=1[F:13].[BH4-].[Li+].C[Si](Cl)(C)C.CO>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][C:3]=1[F:13]

Participants

7

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 668017121-Chloro-2-fluoro-4-(2-nitro-vinyl)-benzene

Product 1

HCID 193623072-(4-Chloro-3-fluorophenyl)ethylamineYield 115.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-Chloro-2-fluoro-4-(2-nitro-vinyl)-benzene (I-33a: 1.1 g, 4.97 mmol) in dry THF (8 mL) was added to a stirred solution of lithium borohydride (433 mg, 19.90 mmol) and trimethylsilyl chloride (5 mL, 39.66 mmol) in dry THF (8 mL) at 0° C. The resulting mixture was stirred at room temperature for 78 hours. The reaction was monitored by TLC (10% methanol in DCM). The reaction mixture was cooled to 0° C., quenched with methanol and concentrated under reduced pressure to afford 1 g of the product (100% yield).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c80980a251a4abda1095df78b7e70ef
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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