Diisopropylcarbodiimide → 4-(Benzyloxy)benzyl (2-bromo-5-fluorophenyl)acetate

HRID 1171883Notes

Reaction equation

HRID 1171883 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH2:25][C:26](O)=[O:27].C(N=C=NC(C)C)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH2:25][C:26]([O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)=[O:27]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 70043(4-(Benzyloxy)phenyl)methanolHCID 27739272-(2-Bromo-5-fluorophenyl)acetic acid

Product 1

HCID 866237744-(Benzyloxy)benzyl (2-bromo-5-fluorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 3 g (2.73 mmol) of Wang resin (p-benzyloxybenzyl alcohol resin, 100-200 mesh) in 49 ml of dichloromethane is stirred (orbital stirring) at room temperature for 15 minutes. 2.8 g (12.0 mmol) of (2-bromo-5-fluorophenyl)acetic acid dissolved in 20 ml of dichloromethane are then added, followed by addition of 0.067 g (0.55 mmol) of 4-dimethylaminopyridine and 1.88 ml (12.0 mol) of N,N′-diisopropylcarbodiimide.

Workup

  1. stirring(orbital stirring) at room temperature for 15 minutes
  2. additionare then added

Sources & evidence

ORD record
ord-418d3fafa14c46bea31126cf9ba3cf3a
Source dataset
uspto-grants-2010_11
Patent number
US07829721B2

Reaction notes

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