Benzoyl chloride, 3-bromo- → HCID 18665553, compound

HRID 2395372Notes

Reaction equation

HRID 2395372 reaction equation
[Br: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>[Br: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 74377Benzoyl chloride, 3-bromo-HCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 18665553HCID 18665553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of 3-bromobenzoyl chloride (13 g, 58 mmol) in dichloromethane (500 ml) was rapidly added a solution of (R)-(-)-2-phenyl-glycinol (10.5 g, 76 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 3 h and insolubles removed by filtration. Concentration of the filtrate gave 2-(3-bromobenzamido)-2(R)-phenylethan-1-ol as colorless solids (18.5 g, quant).

Workup

  1. custominsolubles removed by filtration

Sources & evidence

ORD record
ord-4fa1b44ce6804930990c287eba5323bc
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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