1,2-Dichloroethane → HCID 66606524, compound

HRID 661850Notes

Reaction equation

HRID 661850 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[F:10])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 99352-Fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidineHCID 181649HOAt

Product 1

HCID 66606524HCID 66606524, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Step 1 A mixture of 3-bromo-2-methylaniline (1.66 mL, 13.4 mmol), 2-fluorobenzoic acid (1.883 g, 13.4 mmol), and HOAT (2.74 g, 20.2 mmol) in EtOAc (60 mL) was treated with DIEA (4.7 mL, 26.9 mmol) and EDC (5.15 g, 26.9 mmol) and the mixture was stirred at rt. After 19 h, the mixture was diluted with EtOAc and washed with water, 1 M hydrochloric acid (twice), NaHCO3 (aq) (twice) and brine, dried and concentrated to provide N-(3-bromo-2-methylphenyl)-2-fluorobenzamide as tan fluffy needles (4.11 g, 99%). 1H NMR (400 MHz, chloroform-d) δ 8.34-8.50 (1 H, m), 8.20 (1H, td, J=7.9, 1.8 Hz), 7.96 (1H, d, J=8.1 Hz), 7.50-7.59 (1H, m), 7.44 (1H, dd, J=8.0, 0.8 Hz), 7.30-7.37 (1H, m), 7.21 (1H, dd, J=12.8, 7.9 Hz), 7.12 (1H, t, J=8.0 Hz), 2.45 (3H, s). Mass spectrum m/z 308, 310 (M+H)+.

Workup

  1. washwashed with water, 1 M hydrochloric acid (twice), NaHCO3 (aq) (twice) and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1a793e1d7a54a0b9f03207a160cc00a
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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