3-Iodobenzoyl chloride → HCID 18665555, compound

HRID 2395364Notes

Reaction equation

HRID 2395364 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]1([C@H:17]([CH2:19][OH:20])[NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:18][C@H:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:19][OH:20])=[O:6]

Participants

4

Reactant 2

HCID 743783-Iodobenzoyl chlorideHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 18665555HCID 18665555, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of 3-iodobenzoyl chloride (16.79 g, 63 mmol) in dichloromethane (300 ml) was rapidly added a solution of (R)-(-)-2-phenylglycinol (8.64 g, 63 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 3 hours and crude product collected by filtration. Recrystallization from isopropyl alcohol gave (+)-2-(3-iodobenzamido)-2(R)-phenylethan-1-ol as white needles (14.74 g, 64%).

Workup

  1. filtrationcrude product collected by filtration
  2. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-a72381f5fbc64f4999e5db589a82774b
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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