Chlorotrimethylsilane → 2-(3-Chloro-4-fluorophenyl)ethan-1-amine

HRID 1843908Notes

Reaction equation

HRID 1843908 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[F:13].[BH4-].[Li+].C[Si](Cl)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][C:3]=1[F:13]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 668018422-Chloro-1-fluoro-4-(2-nitro-vinyl)-benzene

Product 1

HCID 224638772-(3-Chloro-4-fluorophenyl)ethan-1-amineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using the same reaction procedure and workup as described in Example 33, 2-Chloro-1-fluoro-4-(2-nitro-vinyl)-benzene (I-34a: 1.7 g, 8.4577 mmol) in dry THF (17 mL) was reacted with lithium borohydride (736.8 mg, 33.8308 mmol) and trimethylsilyl chloride (8.6 mL, 67.6616 mmol) in dry THF (9 mL) to afford 1.3 g of the product (100% yield).

Workup

  1. customthe same reaction procedure

Sources & evidence

ORD record
ord-217d9d13efc2488bb7b72be65b102e38
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…