1-(Bromomethyl)-4-chlorobenzene → HCID 68998824, compound

HRID 750038Notes

Reaction equation

HRID 750038 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68998824HCID 68998824, compoundYield 58%

Procedure

Followed the same procedure as that of step 2 in Example 91 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (150 mg, 0.5 mmol) and 4-chloro-benzyl bromide (125 mg, 0.6 mmol) to afford the title product (120 mg, 58% yield); LCMS; 100% APCI+, Calcd: 417.94. Found m/z: 418.23 (M). 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.80-2.09 (m, 4H), 3.28-3.43 (m, 2H), 3.69-3.91 (m, 1H), 4.02-4.18 (m 2H), 4.97 (s, 2H), 6.86 (s, 4H), 7.35 (s, 4H).

Sources & evidence

ORD record
ord-26eb848dcb724208b8c7529f5c0b2343
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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