2-Chloro-4-fluorobenzaldehyde → HCID 69154961, compound

HRID 2251975Notes

Reaction equation

HRID 2251975 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:15][C:16](=[O:21])[NH:17][CH2:18][CH2:19][NH2:20])([CH3:14])([CH3:13])[CH3:12].[BH4-].[Na+]>CO>[C:11]([O:15][C:16](=[O:21])[NH:17][CH2:18][CH2:19][NH:20][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[Cl:1])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 1450242-Chloro-4-fluorobenzaldehydeHCID 187201N-BOC-ethylenediamineHCID 4311764Sodium borohydride

Product 1

HCID 69154961HCID 69154961, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-4-fluoro-benzaldehyde (742 mg, 4.68 mmol) in MeOH (16 mL), add N-(2-aminoethyl)carbamic acid tert-butyl ester (500 mg, 3.12 mmol) and stir at RT for 4 hours. Cool reaction to 0° C. and slowly add NaBH4 (1.42 g, 37.4 mmol). Allow reaction to slowly warm to RT and stir for 12 hours. Quench reaction with 1N NaOH (80 mL) and extract with CH2Cl2 (40 mL). Dry organic layer over Na2SO4 and concentrate to afford the title compound. Quantitative yield. MS (IS) 303.1 (M+1).

Workup

  1. temperatureCool
  2. customreaction to 0° C.
  3. customAllow reaction
  4. temperatureto slowly warm to RT
  5. stirringstir for 12 hours
  6. customQuench
  7. customreaction with 1N NaOH (80 mL)
  8. extractionextract with CH2Cl2 (40 mL)
  9. concentrationDry organic layer over Na2SO4 and concentrate

Sources & evidence

ORD record
ord-9f61968d11c44cfcb0446576bb06e471
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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