2-Chloro-1,3,2-benzodioxaborole → o-Phenetidine

HRID 1292837Notes

Reaction equation

HRID 1292837 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][CH3:16])(C)(C)C.B1(Cl)OC2C(=CC=CC=2)O1>C(Cl)Cl>[CH2:15]([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH2:7])[CH3:16]

Participants

4

Reactant 2

HCID 41369242-Chloro-1,3,2-benzodioxaboroleHCID 4935495tert-butyl-N-(2-ethoxyphenyl)carbamate

Product 1

HCID 7203o-PhenetidineYield 520.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction between 1.2 g (1.4 mmol) of tert-butyl-N-(2-ethoxyphenyl)carbamate (˜1.2 mmol/g) bonded on solid support 9 and 0.87 g (5.66 mmol, 4 eq) of 0.2 M B-chlorocatecholborane in anhydrous CH2Cl2 according to the procedure described hereinabove, followed by filtration and washing, gave 1 g of a brown powder (yield: 95%).

Workup

  1. filtrationfollowed by filtration
  2. washwashing

Sources & evidence

ORD record
ord-4515da28b6fb40278be91db9bd8cc800
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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