Dimethylformamide → Tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate

HRID 1896613

Reaction equation

HRID 1896613 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.CN(C=O)C>O>[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 59418705Tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 3-hydroxyphenylcarbamate (0.245 g, 1.17 mmol), K2CO3 (404 mg, 2.93 mmol), and 3-bromobenzyl bromide (322 mg, 1.29 mmol) was added anhydrous DMF (5 mL). The reaction mixture was heated to 60° C. for 18 hours. The reaction mixture was cooled to rt, poured into water and the resulting precipitate was collected by filtration and washed with water to provide the desired product tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate (34A) with sufficient purity for subsequent use.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-94bb1667a57f46eb981a0628217bd1d1
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Linked notes

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