Carbon tetrabromide → N-[Bromomethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester

HRID 383158Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10](CO)=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].[C:28]([Br:32])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:28][Br:32])[C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

Conditions

Temperature: -10 °C

Procedure

To a stirred solution at −10° C. under N2 of N-[4-hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester (200 mg, 0.517 mmol ), prepared as in Example 403F, and carbon tetrabromide (189 mg, 0.568 mmol) in CH2Cl2 (5 mL) was added triphenylphosphine (163 mg, 0.620 mmol). Reaction stirred one hour at −10° C., and then, solvents concentrated in vacuo to produce a colorless glass. The residue could not be stored, and so, was used directly in the reaction in Example 1188B.

Workup

customReaction
concentrationsolvents concentrated in vacuo
customto produce a colorless glass
customso, was used directly in the reaction in Example 1188B

Sources & evidence

ORD record: ord-73b1fa7a316d40e3a8a5a23554bc9d61
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310095B1

Reaction notes

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